Ammonia → Benzyl rac-alpha-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamate

HRID 275596노트

반응식

HRID 275596 반응식
[CH2:1]([O:8][C:9]([CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][S:13]([C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18])(=[O:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:29]>O1CCCC1.C(OCC)(=O)C>[C:17]([C:16]([S:13]([CH2:12][CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])(=[O:15])=[O:14])([CH3:21])[CH3:20])(=[O:18])[NH2:29]

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 20088482(RS)-2-[[2-[(Benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride

생성물 1

HCID 54066967Benzyl rac-alpha-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamate수율 91.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 1.05 g (2.5 mmol) of crude (RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride in 29 ml (9.3 mmol) of 0.32M ammonia in tetrahydrofuran was stirred at room temperature for 5 hours. Subsequently, the reaction solution was diluted with 40 ml of ethyl acetate and extracted with 20 ml of 1N hydrochloric acid. The ethyl acetate extract was then washed with 20 ml of saturated sodium hydrogen carbonate solution and 20 ml of saturated sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. There was obtained 0.92 g of benzyl rac-α-[[(1-carbamoyl-1-methylethyl)sulfonyl]methyl]hydrocinnamate as a colourless solid, MS: 312 (M-benzyl)+.

후처리

  1. extractionextracted with 20 ml of 1N hydrochloric acid
  2. extractionThe ethyl acetate extract
  3. washwas then washed with 20 ml of saturated sodium hydrogen carbonate solution and 20 ml of saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-b20e8a71151b418ba7255c812bf9299e
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393875

반응 노트

불러오는 중…