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

HRID 1278408Notes

Reaction equation

HRID 1278408 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-ba01e249f852415ebcd42f18324507c1
Source dataset
uspto-grants-1981_07
Patent number
US04281018

Reaction notes

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