NOVEL METHOD FOR PRODUCING HYDROXAMIC ACID DERIVATIVE, AND INTERMEDIATE THEREFOR

1 . A method for producing a compound represented by formula [2], comprising:

deprotecting a compound represented by the formula [1]:

wherein R 1 represents a C 1-3 alkyl group; R 2 represents a C 1-3 alkyl group; and R 3a represents a hydroxyl-protecting group

to produce the compound represented by formula [2]:

2 . The production method according to claim 1 , wherein the deprotecting of the compound represented by the formula [1] comprises:

(1) deprotecting the hydroxyl-protecting group in the compound represented by the formula [1] to obtain a compound represented by the formula [3]:

wherein R 1 represents a C 1-3 alkyl group; and R 2 represents a C 1-3 alkyl group; and

(2) deprotecting the compound represented by the formula [3] to obtain the compound represented by formula [2]:

3 . The production method according to claim 1 , wherein R 1 is a methyl group; and R 2 is a methyl group.

4 . The production method according to claim 1 , wherein R 3a is a tetrahydropyranyl group.

5 . A method for producing a compound represented by formula [2], comprising:

reacting a compound represented by the formula [4]:

wherein R 1 represents a C 1-3 alkyl group; and R 2 represents a C 1-3 alkyl group with a compound represented by the formula [5]:

wherein R 3a represents a hydroxyl-protecting group; and L 1 represents a leaving group to obtain a compound represented by the formula [1]:

wherein R 1 , R 2 , and R 3a are as defined above; and

deprotecting the obtained compound represented by the formula [1] to produce the compound represented by formula [2]:

6 . The production method according to claim 5 , wherein the deprotecting of the compound represented by the formula [1] comprises:

(1) deprotecting the hydroxyl-protecting group in the compound represented by the formula [1] to obtain a compound represented by the formula [3]:

wherein R 1 represents a C 1-3 alkyl group; and R 2 represents a C 1-3 alkyl group; and

(2) deprotecting the compound represented by the formula [3] to obtain the compound represented by formula [2]:

7 . The production method according to claim 5 , wherein R 1 is a methyl group; and R 2 is a methyl group.

8 . The production method according to claim 5 , wherein R 3a is a tetrahydropyranyl group; and L 1 is an iodine atom.

9 . A method for producing a compound represented by formula [2], comprising:

reducing a compound represented by the formula [6]:

wherein R 4 represents an optionally substituted acyl group to obtain a compound represented by the formula [7]:

wherein R 4 is as defined above;

deprotecting the obtained compound represented by the formula [7] to obtain a compound represented by formula [8]:

reacting the obtained compound represented by formula [8] with a compound represented by the formula [9]:

wherein R 5a represents a silyl group

to obtain a compound represented by the formula [10]:

wherein R 5a is as defined above;

deprotecting the obtained compound represented by the formula [10] to obtain a compound represented by formula [11]:

protecting the diol group in the obtained compound represented by formula [11] to obtain a compound represented by the formula [4]:

wherein R 1 represents a C 1-3 alkyl group; and R 2 represents a C 1-3 alkyl group;

reacting the obtained compound represented by the formula [4] with a compound represented by the formula [5]:

wherein R 3a represents a hydroxyl-protecting group; and L 1 represents a leaving group to obtain a compound represented by the formula [1]:

wherein R 1 , R 2 , and R 3a are as defined above; and

deprotecting the obtained compound represented by the formula [1] to produce the compound represented by formula [2]:

10 . The production method according to claim 9 , wherein the deprotecting of the compound represented by the formula [1] comprises:

(1) deprotecting the hydroxyl-protecting group in the compound represented by the formula [1] to obtain a compound represented by the formula [3]:

wherein R 1 represents a C 1-3 alkyl group; and R 2 represents a C 1-3 alkyl group; and

(2) deprotecting the compound represented by the formula [3] to obtain the compound represented by formula [2]:

11 . The production method according to claim 9 , wherein R 4 is an acetyl group; and R 5a is a trimethylsilyl group.

12 . The production method according to claim 9 , wherein R 1 is a methyl group; and R 2 is a methyl group.

13 . The production method according to claim 9 , wherein R 3a is a tetrahydropyranyl group; and L 1 is an iodine atom.

14 . A method for producing a compound represented by formula [8], comprising:

reducing a compound represented by the formula [6]:

wherein R 4 represents an optionally substituted acyl group

to obtain a compound represented by the formula [7]:

wherein R 4 is as defined above; and

deprotecting the obtained compound represented by the formula [7] to produce the compound represented by formula [8]:

15 . The production method according to claim 14 , wherein R 4 is an acetyl group.

16 . A compound represented by the formula [12]:

wherein R 1 represents a C 1-3 alkyl group; R 2 represents a C 1-3 alkyl group; and R 5 represents a hydrogen atom, a group represented by the formula [13]:

wherein R 6 represents a C 1-3 alkyl group; R 7 represents a C 1-3 alkyl group; or R 6 and R 7 together represent a C 3-6 alkylene group; and * represents a binding position, or

a group represented by the formula [14]:

wherein R 3 represents a hydrogen atom or a hydroxyl-protecting group; and * represents a binding position.

17 . The compound according to claim 16 , wherein R 1 is a methyl group; R 2 is a methyl group; and R 5 is a hydrogen atom.

18 . The compound according to claim 16 , wherein R 1 is a methyl group; R 2 is a methyl group; and R 5 is a group represented by the formula [14]:

wherein R 3 represents a hydrogen atom or a hydroxyl-protecting group; and * represents a binding position.

19 . The compound according to claim 18 , wherein R 3 is a hydrogen atom or a tetrahydropyranyl group.