IP Library Granted Patent US 8,546,534
Granted Patent B2
US 8,546,534 · App. 13/220,841 · Granted Oct 1, 2013

Branched chain-containing aromatic compound

Inventor: Daisuke Takahashi (Mie, JP)
Assignee: Ajinomoto Co., Inc.
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,546,534
App. No.
13/220,841
Granted
Oct 1, 2013
Kind
B2
Abstract

The present invention provides a particular branched chain-containing aromatic compound. The branched chain-containing aromatic compound of the present invention is easily-soluble in isopropyl acetate superior in liquid-separation operability, and can be used for a production method of peptide and the like, which provides a final product simply by extraction separation, without crystallization and isolation of each intermediate in each step.

Claims (207)

1. A branched chain-containing aromatic compound represented by formula (I):

wherein

each Q is independently a single bond, or —O—, —S—, —C(═O)O—, —C(═O)NH— or —NH—;

each R a is independently an organic group having at least one aliphatic hydrocarbon group having one or more branched chains, wherein a total number of branched chains in each R a is not less than 3 and a total carbon number in each R a is not less than 17 and not more than 300 and is a group represented by the formula (c):

wherein

* indicates the bonding position to Q;

R 5 and R 6 are both hydrogen atoms, or taken together to are ═O;

n 0 is an integer of 2 to 40;

each R 7 and R 8 is independently a hydrogen atom or a C 1-4 alkyl group;

each X 2 is independently a single bond or a C 1-4 alkylene group; and

R 9 is a hydrogen atom or a C 1-4 alkyl group;

R 10 is a C 1-4 alkyl group or the formula (I′):

wherein

* indicates the bonding position;

other symbols are as defined above, and

ring A′ optionally has, in addition to R 1 , Q, and C(X)(Y)Z, one or more substituents selected from the group consisting of a halogen atom, a C 1-6 alkyl group optionally substituted by one or more halogen atoms, and a C 1-6 alkoxy group optionally substituted by one or more halogen atoms,

provided that R 7 and R 8 are not hydrogen atoms at the same time, and when n 0 is 2, R 9 is a C 1-4 alkyl group;

k is an integer of 1 to 4;

R 1 is a hydrogen atom

ring A optionally further has, in addition to R 1 , (QR a ) k , and C(X)(Y)Z, one or more substituents selected from the group consisting of a halogen atom, a C 1-6 alkyl group optionally substituted by one or more halogen atoms, and a C 1-6 alkoxy group optionally substituted by one or more halogen atoms;

X is a hydrogen atom or a phenyl group;

Y is a hydroxyl group or an —NHR group (wherein R is a hydrogen atom, an alkyl group, or an aralkyl group); and

Z is a hydrogen atom or a group represented by formula (a):

wherein

* indicates the bonding position;

m is an integer of 0 to 4;

each Q is as defined above;

each R b is independently an organic group having at least one aliphatic hydrocarbon group having one or more branched chains, wherein a total number of the branched chain in each R b is not less than 3 and a total carbon number in each R b is not less than 17 and not more than 300;

R 2 is a hydrogen atom; and

ring B optionally further has, in addition to (QR b ) m and R 2 , one or more substituents selected from the group consisting of a halogen atom, a C 1-6 alkyl group optionally substituted by one or more halogen atoms, and a C 1-6 alkoxy group optionally substituted by one or more halogen atoms;

wherein said organic group having at least one aliphatic hydrocarbon group having one or more branched chains, a total number of the branched chain of not less than 3 and a total carbon number of not less than 17 and not more than 300 for each R b is a group having 3 or more of the same or different divalent groups represented by formula (b):

wherein

* indicates the bonding position with the adjacent atom;

R 3 and R 4 are each independently a hydrogen atom or a C 1-4 alkyl group;

X 1 is a single bond, a C 1-4 alkylene group, or an oxygen atom,

provided that R 3 and R 4 are not hydrogen atoms at the same time.

2. A branched chain-containing aromatic compound according to claim 1 , wherein said organic group having at least one aliphatic hydrocarbon group having one or more branched chains, a total number of the branched chain of not less than 3 and a total carbon number of not less than 17 and not more than 300 for each R b is a group represented by the formula (c):

wherein

* indicates the bonding position to Q;

R 5 and R 6 are both hydrogen atoms, or taken together to are ═O;

n 0 is an integer of 2 to 40;

each R 7 and R 8 is independently a hydrogen atom or a C 1-4 alkyl group;

each X 2 is independently a single bond or a C 1-4 alkylene group; and

R 9 is a hydrogen atom or a C 1-4 alkyl group;

R 10 is a C 1-4 alkyl group or the formula (I′):

wherein

* indicates the bonding position;

other symbols are as defined above, and

ring A′ optionally has, in addition to R 1 , Q, and C(X)(Y)Z, one or more substituents selected from the group consisting of a halogen atom, a C 1-6 alkyl group optionally substituted by one or more halogen atoms, and a C 1-6 alkoxy group optionally substituted by one or more halogen atoms,

provided that R 7 and R 8 are not hydrogen atoms at the same time, and when n 0 is 2, R 9 is a C 1-4 alkyl group.

3. A branched chain-containing aromatic compound according to claim 2 , wherein, in said formula (c),

R 5 and R 6 are both hydrogen atoms;

each R 7 and R 8 is independently a hydrogen atom, a methyl group or an ethyl group;

each X 2 is independently a single bond, a methylene group or an ethylene group; and

R 9 is a hydrogen atom, a methyl group or an ethyl group.

4. A branched chain-containing aromatic compound according to claim 1 , wherein said organic group having at least one aliphatic hydrocarbon group having one or more branched chains, a total number of the branched chain of not less than 3 and a total carbon number of not less than 17 and not more than 300 for each R b is a group represented by formula (d):

wherein

* indicates the bonding position to Q;

each OR 11 is independently a hydroxyl group substituted by a group represented by the formula (c′):

wherein

* indicates the bonding position to O;

R 5 and R 6 are both hydrogen atoms, or taken together form ═O;

n 0 is an integer of 2 to 40;

each R 7 and R 8 is independently a hydrogen atom or a C 1-4 alkyl group;

each X 2 is independently a single bond or a C 1-4 alkylene group; and

R 9 is a hydrogen atom or a C 1-4 alkyl group;

R 10 is a C 1-4 alkyl group or a group represented by formula (I′):

wherein

* indicates the bonding position;

other symbols are as defined above, and

ring A′ optionally has, in addition to R 1 , Q*, and C(X)(Y)Z, one or more substituents selected from the group consisting of a halogen atom, a C 1-6 alkyl group optionally substituted by one or more halogen atoms, and a C 1-6 alkoxy group optionally substituted by one or more halogen atoms,

provided that R 7 and R 8 are not hydrogen atoms at the same time, and when n 0 is 2, R 9 is a C 1-4 alkyl group; and

m 1 is an integer of 1 to 3.

5. A branched chain-containing aromatic compound according to claim 1 , wherein said organic group having at least one aliphatic hydrocarbon group having one or more branched chains, a total number of the branched chain of not less than 3 and a total carbon number of not less than 17 and not more than 300 for each R b is a group represented by formula (e):

wherein

* indicates the bonding position to Q;

n 1 is an integer of 1 to 10;

n 2 is an integer of 1 to 10;

each R 15 and R 16 is independently a hydrogen atom or a C 1-4 alkyl group;

each X 3 is independently a single bond or a C 1-4 alkylene group;

each R 17 and R 18 is independently a hydrogen atom or a C 1-4 alkyl group;

each X 5 is independently a single bond or a C 1-4 alkylene group;

X 4 is a single bond or a C 1-4 alkylene group; and

R 12 , R 13 , R 14 , R 19 , R 20 and R 21 are each independently a hydrogen atom or a C 1-4 alkyl group,

provided when R 15 and R 16 , and/or R 17 and R 18 are not hydrogen atoms at the same time, and when n 1 +n 2 is 2, then two or more of R 12 , R 13 and R 14 are each independently a C 1-4 alkyl group, or two or more of R 19 , R 20 and R 21 are each independently a C 1-4 alkyl group.

6. A branched chain-containing aromatic compound according to claim 5 , wherein, in said formula (e),

n 1 is an integer of 1 to 5;

n 2 is an integer of 1 to 5;

each R 15 and R 16 is independently a hydrogen atom, a methyl group or an ethyl group;

each X 3 is independently a single bond, a methylene group, or an ethylene group;

each R 17 and R 18 is independently a hydrogen atom, a methyl group, or an ethyl group;

each X 5 is independently a single bond, a methylene group, or an ethylene group; and

X 4 is a single bond, a methylene group, or an ethylene group.

7. A branched chain-containing aromatic compound according to claim 6 , wherein, in said formula (e),

each R 15 and R 16 is independently a hydrogen atom or a methyl group;

each X 3 is independently a single bond or a methylene group;

each R 17 and R 18 is independently a hydrogen atom or a methyl group;

each X 5 is independently a single bond or a methylene group;

X 4 is a single bond or a methylene group; and

R 12 , R 13 , R 14 , R 19 , R 20 and R 21 are each a methyl group.

8. A branched chain-containing aromatic compound according to claim 1 , wherein each R a is independently a

3,7,11,15-tetramethylhexadecyl group;

a 2,2,4,8,10,10-hexamethyl-5-dodecanoyl group;

a group represented by formula (f):

wherein

* indicates the bonding position to Q,

n 10 is 23 to 34,

R 10 is a group represented by formula (I′):

wherein

* indicates the bonding position, and

other symbols are as defined above,

wherein ring A′ optionally has, in addition to R 1 , Q*, and C(X)(Y)Z, one or more substituents selected from the group consisting of a halogen atom, a C 1-6 alkyl group optionally substituted by one or more halogen atoms, and a C 1-6 alkoxy group optionally substituted by one or more halogen atoms;

9. A branched chain-containing aromatic compound according to claim 1 , wherein X and Z are both hydrogen atoms.

10. A branched chain-containing aromatic compound according to claim 1 , wherein X is a hydrogen atom, k is 1, and Z is a group represented by formula (a), wherein R 2 is a hydrogen atom, and m is 0.

11. A branched chain-containing aromatic compound according to claim 1 , wherein Q is —O—.

12. A branched chain-containing aromatic compound according to claim 1 , wherein Y is a hydroxyl group.

13. A branched chain-containing aromatic compound according to claim 1 , wherein Y is an —NHR group.

14. A branched chain-containing aromatic compound according to claim 1 , which is selected from the group consisting of:

2,4-di(2′,3′-dihydrophytyloxy)benzyl alcohol;

3,5-di(2′,3′-dihydrophytyloxy)benzyl alcohol;

4-(2′,3′-dihydrophytyloxy)benzyl alcohol;

1-[(2-chloro-5-(2′,3′-dihydrophytyloxy)phenyl)]-1-phenylmethanamine;

3,4,5-tri(2′,3′-dihydrophytyloxy)benzyl alcohol;

3,4,5-tri(2′,3′-dihydrophytyloxy)benzylamine;

4-(2′,3′-dihydrophytyloxy)benzylamine;

4-(2′,3′-dihydrophytyloxy)-2-methoxybenzyl alcohol;

4-(2′,3′-dihydrophytyloxy)-2-methoxybenzylamine;

4-(2′,3′-dihydrophytyloxy)-2-methylbenzyl alcohol;

4-(2′,3′-dihydrophytyloxy)-2-methylbenzylamine;

a compound represented by the formula:

wherein n 16 is 23 or 34;

a compound represented by the formula:

wherein n 17 is 23 or 34;

15. A branched chain-containing aromatic compound according to claim 1 , which has a saturation solubility in isopropyl acetate (100 g) at 20° C. of 1 to 95 wt %.

16. A branched chain-containing aromatic compound according to claim 1 , which has a saturation solubility in isopropyl acetate (100 g) at 20° C. of 10-95 wt %.

17. A branched chain-containing aromatic compound represented by formula (I):

wherein

each Q is independently a single bond, or —O—, —S—, —C(═O)O—, —C(═O)NH— or —NH—;

each R a is independently an organic group having at least one aliphatic hydrocarbon group having one or more branched chains, wherein a total number of branched chains in each R a is not less than 3 and a total carbon number in each R a is not less than 17 and not more than 300 and is a group represented by the formula (c):

wherein

* indicates the bonding position to Q;

R 5 and R 6 are both hydrogen atoms, or taken together to are ═O;

n 0 is an integer of 2 to 40;

each R 7 and R 8 is independently a hydrogen atom or a C 1-4 alkyl group;

each X 2 is independently a single bond or a C 1-4 alkylene group; and

R 9 is a hydrogen atom or a C 1-4 alkyl group;

R 10 is a C 1-4 alkyl group or the formula (I′):

wherein

* indicates the bonding position;

other symbols are as defined above, and

ring A′ optionally has, in addition to R 1 , O, and C(X)(Y)Z, one or more substituents selected from the group consisting of a halogen atom, a C 1-6 alkyl group optionally substituted by one or more halogen atoms, and a C 1-6 alkoxy group optionally substituted by one or more halogen atoms,

provided that R 7 and R 8 are not hydrogen atoms at the same time, and when n 0 is 2, R 9 is a C 1-4 alkyl group;

k is an integer of 1 to 4;

R 1 is a hydrogen atom;

ring A optionally further has, in addition to R 1 , (QR a ) k , and C(X)(Y)Z, one or more substituents selected from the group consisting of a halogen atom, a C 1-6 alkyl group optionally substituted by one or more halogen atoms, and a C 1-6 alkoxy group optionally substituted by one or more halogen atoms;

X is a hydrogen atom or a phenyl group;

Y is a hydroxyl group, an —NHR group (wherein R is a hydrogen atom, an alkyl group, or an aralkyl group), or a halogen atom; and

Z is a hydrogen atom or a group represented by formula (a):

wherein

* indicates the bonding position;

m is an integer of 0 to 4;

each Q is as defined above;

each R b is independently an organic group having at least one aliphatic hydrocarbon group having one or more branched chains, wherein a total number of the branched chain in each R b is not less than 3 and a total carbon number in each R b is not less than 17 and not more than 300;

R 2 is a hydrogen atom; and

ring B optionally further has, in addition to (QR b ) m and R 2 , one or more substituents selected from the group consisting of a halogen atom, a C 1-6 alkyl group optionally substituted by one or more halogen atoms, and a C 1-6 alkoxy group optionally substituted by one or more halogen atoms;

wherein said organic group having at least one aliphatic hydrocarbon group having one or more branched chains, a total number of the branched chain of not less than 3 and a total carbon number of not less than 17 and not more than 300 for each R b is a group having 3 or more of the same or different divalent groups represented by formula (b):

wherein

* indicates the bonding position with the adjacent atom;

R 3 and R 4 are each independently a hydrogen atom or a C 1-4 alkyl group;

X 1 is a single bond, a C 1-4 alkylene group, or an oxygen atom,

provided that R 3 and R 4 are not hydrogen atoms at the same time.

18. A branched chain-containing aromatic compound according to claim 1 , wherein each R a has a total carbon number of not less than 18.

19. A branched chain-containing aromatic compound according to claim 1 , wherein each R a has a total carbon number of not less than 19.

20. A branched chain-containing aromatic compound according to claim 1 , wherein each R a has a total carbon number of not less than 20.

21. A branched chain-containing aromatic compound according to claim 1 , wherein k is an integer of 2 to 4.

22. A branched chain-containing aromatic compound according to claim 1 , wherein k is an integer of 3 to 4.

23. A branched chain-containing aromatic compound according to claim 1 , wherein a total number of the branched chain in each R b is not less than 4.

24. A branched chain-containing aromatic compound according to claim 1 , wherein each R b is independently a

3,7,11,15-tetramethylhexadecyl group;

a 2,2,4,8,10,10-hexamethyl-5-dodecanoyl group;

a 3,4,5-tri(3′,7′,11′,15′-tetramethylhexadecyloxy)benzyl group;

a 3,5-di(3′,7′,11′,15′-tetramethylhexadecyloxy)benzyl group;

a group represented by formula (f):

wherein

* indicates the bonding position to Q,

n 10 is 23 to 34,

R 10 is a group represented by formula (I′):

wherein

* indicates the bonding position, and

other symbols are as defined above,

wherein ring A′ optionally has, in addition to R 1 , Q*, and C(X)(Y)Z, one or more substituents selected from the group consisting of a halogen atom, a C 1-6 alkyl group optionally substituted by one or more halogen atoms, and a C 1-6 alkoxy group optionally substituted by one or more halogen atoms;

a group represented by formula (g):

wherein

* indicates the bonding position to Q, and

n 11 is 1 to 10;

a group represented by formula (h):

wherein

* indicates the bonding position to Q, and

n 12 is 2 to 10;

a group represented by formula (I):

wherein

* indicates the bonding position to Q, and

n 13 and n 14 are each independently 1 to 10; or

a group represented by formula (j):

wherein

* indicates the bonding position to Q, and

n 15 is 2 to 20.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 14, 2011
From: TAKAHASHI, DAISUKE
To: AJINOMOTO CO., INC.
Reel/Frame 027221/0715 →
Priority Claims (1)
JP 2010-192961 · Aug 30, 2010 · national
Continuity (2)
Provisional Application 61378170 · Aug 30, 2010
Related Publication 20120059149A1 · Mar 8, 2012