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

HRID 1388127Notes

Reaction equation

HRID 1388127 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 product 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°

Workup

  1. customExcess ammonia is removed in vacuo
  2. extractionthe by-product, benzamide, is extracted with ethyl acetate
  3. extractionthe product 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-eb7f1adbe401431aa692af0396f9aa41
Source dataset
uspto-grants-1984_02
Patent number
US04430344

Reaction notes

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