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Water → HCID 70047752, 화합물

HRID 1080921
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HRID 1080921 반응식
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH2:22]([O:29][C:30]([NH:32][C@H:33]([C:37]([NH:39][C@@H:40]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C@H:41]([OH:56])[CH2:42][C@@H:43]1[CH2:48][CH2:47][CH2:46][CH2:45][C@H:44]1[C:49]([NH:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:38])[CH:34]([CH3:36])[CH3:35])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C)C=O>[CH2:22]([O:29][C:30]([NH:32][C@H:33]([C:37]([NH:39][C@@H:40]([CH2:57][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[C:41](=[O:56])[CH2:42][C@@H:43]1[CH2:48][CH2:47][CH2:46][CH2:45][C@H:44]1[C:49]([NH:51][C:52]([CH3:54])([CH3:55])[CH3:53])=[O:50])=[O:38])[CH:34]([CH3:36])[CH3:35])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 70049680HCID 70049680, 화합물

생성물 1

HCID 70047752HCID 70047752, 화합물수율 67.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

220 mg (0.59 mmol) of pyridinium dichromate were added to a solution of 48 mg (0.08 mmol) of 2(S)-[3(S)-[[N-(benzyloxycarbonyl)-L-valyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-1(R)-cyclohexanecarboxamide in 1 ml of dimethylformamide and the mixture was stirred at room temperature for 18 hours. 10 ml of water were added and the mixture was extracted with two 10 ml portions of ethyl acetate. The combined extracts were washed with two 10 ml portions of water, dried over anhydrous magnesium sulphate and evaporated; The crude product was chromatographed on a column of silica gel using 4% methanol in dichloromethane for the elution to give 31 mg of 2(S)-[3(S)-[[N-(benzyloxycarbonyl)-L-valyl]amino]-2-oxo-4-phenylbutyl]-N-tert.butyl-1(R)-cyclohexanecarboxamide as a white solid of melting point 186°-188° C.; MS m/e 578 [M+H]+.

후처리

  1. extractionthe mixture was extracted with two 10 ml portions of ethyl acetate
  2. washThe combined extracts were washed with two 10 ml portions of water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated
  5. customThe crude product was chromatographed on a column of silica gel using 4% methanol in dichloromethane for the elution

출처 및 근거

ORD 기록
ord-fa76277aa0db4e278f1cc32c0fc7d589
출처 데이터셋
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05583248

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