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

HRID 223708노트

반응식

HRID 223708 반응식
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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 222Ammonia용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4bb18fd9afa0444488af5f1cefbcd2b1
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04356183

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