3-[4-(16-Bromohexadecylamino)benzoyl]-4-carbethoxythiazolidine → 3-[4-(15-Carbomethoxypentadecylamino)benzoyl]-4-carboxythiazolidine

HRID 904263Notes

Reaction equation

HRID 904263 reaction equation
BrC[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:37](=[O:40])([OH:39])[O-].[Na+].[CH3:42]C(C)=O>>[C:37]([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)([O:39][CH3:42])=[O:40]

Participants

3

Reactant 2

HCID 130254093-[4-(16-Bromohexadecylamino)benzoyl]-4-carbethoxythiazolidineHCID 86737261Acetone sodium bicarbonate

Product 1

HCID 211632443-[4-(15-Carbomethoxypentadecylamino)benzoyl]-4-carboxythiazolidine

Procedure

One-tenth mole of 4-(15-carbomethoxypentadecylamino)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-a495905947c44a7ca6455c74124765b2
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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