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

HRID 1106165Notes

Reaction equation

HRID 1106165 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-ad9c8afb3d4244bfa23b918532e1c3db
Source dataset
uspto-grants-1982_01
Patent number
US04311846

Reaction notes

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