(4R)-3-(S-Benzoyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid → (4R)-2-(2-Hydroxyphenyl)-3-(3-mercaptopropanoyl)-4-thiazolidinecarboxylic acid

HRID 1462003Notes

Reaction equation

HRID 1462003 reaction equation
C([S:9][CH2:10][CH2:11][C:12]([N:14]1[C@H:18]([C:19]([OH:21])=[O:20])[CH2:17][S:16][CH:15]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28])=[O:13])(=O)C1C=CC=CC=1>N>[OH:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH:15]1[N:14]([C:12](=[O:13])[CH2:11][CH2:10][SH:9])[C@H:18]([C:19]([OH:21])=[O:20])[CH2:17][S:16]1

Participants

3

Reactant 1

HCID 12915688(4R)-3-(S-Benzoyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid

Product 1

HCID 13019472(4R)-2-(2-Hydroxyphenyl)-3-(3-mercaptopropanoyl)-4-thiazolidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To 4.2 g of (4R)-3-(S-benzoyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid, 40 ml of conc. ammonia is added and this solution is stirred at room temperature for 1 hour. Excess ammonia is removed in vacuo and the by-product, benzamide, is extracted with ethyl acetate. The aqueous layer is acidified with dilute hydrochloric acid and the produced oil is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried over anhydrous sodium sulfate, and concentrated to dryness in vacuo to give the titled compound, yield 2.2 g (70%), mp. 146°-148° C. (ethyl acetate), [α]D26 +176° (c=1.0, methanol).

Workup

  1. customExcess ammonia is removed in vacuo
  2. extractionthe by-product, benzamide, is extracted with ethyl acetate
  3. extractionthe produced oil is extracted with ethyl acetate
  4. washThe ethyl acetate layer is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-0013379921194514853a03bac692da20
Source dataset
uspto-grants-1984_07
Patent number
US04457935

Reaction notes

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