IP Library Granted Patent US 7,294,743
Granted Patent B2
US 7,294,743 · App. 10/572,294 · Granted Nov 13, 2007

Method for synthesis of acrylamide derivatives

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Quick Facts
Patent No.
US 7,294,743
App. No.
10/572,294
Granted
Nov 13, 2007
Kind
B2
Abstract

The present invention relates to a method for synthesis of an acrylamide derivative, starting with dissolving a salt of a nucleophilic amine in water to form an aqueous solution and desalting said solution with a base, comprising the following steps: a) addition of dissolved activated acrylic acid derivative to said solution; b) acidification of aqueous phase; and c) extraction of said aqueous phase.

Claims (22)

1. A method for synthesis of an acrylamide derivative, starting with dissolving a salt of a nucleophilic amine in water to form an aqueous solution and desalting said solution with a base, comprising the following steps:

a) addition of dissolved activated acrylic acid derivative to said solution;

b) acidification of aqueous phase; and

c) extraction of said aqueous phase.

2. The method of claim 1 , wherein the acrylamide derivative is an immobiline.

3. The method of claim 2 , wherein the acrylamide derivative is acrylamido agmatine.

4. The method of claim 3 , wherein the salt is an agmatine salt.

5. The method of claim 1 , wherein the extraction in step c) is performed with an organic solvent.

6. The method of claim 5 , wherein the organic solvent is MIBK (methyl isobutyl ketone).

7. The method of claim 1 , wherein the acrylic acid derivative is an activated acrylic acid derivative selected from the group consisting of acryloyl chloride, acrylic acid N-hydroxysuccinimide ester, pentafluorophenyl acrylate, pentachlorophenylacrylate, and 4-nitrophenyl acrylate.

8. The method of claim 1 , wherein the desalting is with NaOH, TEA (triethylamine), DIPEA (diisopropylethylamine), or K 2 CO 3 .

9. The method of claim 1 , further comprising fixing pH to 7.

10. The method of claim 1 , comprising, before step b),

i) basification of aqueous phase to a pH above the pKa of the organic base, and

ii) extraction of aqueous phase with an organic solvent to remove the organic base.

11. The method of claim 1 , wherein agmatine sulphate is dissolved, desalted with K 2 CO 3 and comprising the following steps:

a) addition of acryloyl chloride;

b) acidification to pH 1-4;

c) filtration;

d) extraction with MIBK; and

e) pH adjustment to pH 7.

12. The method of claim 11 , wherein the acidification pH is 2.3.

Assignments (2)
CHANGE OF NAME Recorded Oct 5, 2020
From: GE HEALTHCARE BIO-SCIENCES AB
To: CYTIVA SWEDEN AB
Reel/Frame 054262/0184 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2006
From: ALGOTSSON, MATTIAS; BUSSON, PHILIPPE; THEVENIN, NICOLAS
To: GE HEALTHCARE BIO-SCIENCES AB
Reel/Frame 017397/0242 →