3-[4-(16-Bromohexadecylamino)benzoyl]-4-carbethoxythiazolidine → 3-[4-(16-Bromohexadecylamino)benzoyl]-4-carboxythiazolidine

HRID 1389658Notes

Reaction equation

HRID 1389658 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:36]=[CH:35][C:22]([C:23]([N:25]2[CH:29]([C:30]([O:32]CC)=[O:31])[CH2:28][S:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1>C(=O)(O)[O-].[Na+].CC(C)=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([N:25]2[CH:29]([C:30]([OH:32])=[O:31])[CH2:28][S:27][CH2:26]2)=[O:24])=[CH:35][CH:36]=1

Participants

3

Reactant 1

HCID 130254093-[4-(16-Bromohexadecylamino)benzoyl]-4-carbethoxythiazolidine

Product 1

HCID 130254103-[4-(16-Bromohexadecylamino)benzoyl]-4-carboxythiazolidine

Reagents, catalysts & solvents 1

HCID 86737261Acetone sodium bicarbonateSolvent

Procedure

One-tenth mole of 4-(16-bromohexadecylamino)benzoyl chloride hydrochloride in methylene chloride is added to a solution of 0.1 mole of ethyl thiazolidine-4-carboxylate in chloroform containing two equivalents of triethylamine. After 5 hours at 20° C. the solution is filtered and evaporated to a white solid which is recrystallized from acetonitrile to yield 3-[4-(16-bromohexadecylamino)benzoyl]-4-carbethoxythiazolidine. By means of the alkaline hydrolysis method of Example 10, the ethyl ester is converted to the subject carboxylic acid. This acid is also prepared using the procedure of this Example except that the acylation of the thiazolidine-4-carboxylic acid is carried out in aqueous acetone sodium bicarbonate solution.

Workup

  1. customBy means of the alkaline hydrolysis method of Example 10
  2. customThis acid is also prepared

Sources & evidence

ORD record
ord-32036b50b98843e3b4bb8b489855ede7
Source dataset
uspto-grants-1981_01
Patent number
US04245097

Reaction notes

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