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Hydrochloric Acid → 2-[(1R,2S)-1-acetoxy-2-{(S)-2-cyclohexylmethoxycarbonylamino-4-methylvalerylamino}-3-methylbutyl]-3-phenylcyclopropenone

HRID 36742
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HRID 36742 반응식
[CH:1]1([CH2:7][O:8][C:9]([NH:11][C@@H:12]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:13]([NH:15][C@@H:16]([CH:29]([CH3:31])[CH3:30])[C@@H:17]([C:19]2[C:20](=[O:28])[C:21]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[OH:18])=[O:14])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:36](Cl)(=[O:38])[CH3:37].Cl>C(Cl)Cl.C(N(CC)CC)C>[C:36]([O:18][C@H:17]([C:19]1[C:20](=[O:28])[C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@@H:16]([NH:15][C:13](=[O:14])[C@@H:12]([NH:11][C:9]([O:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:10])[CH2:32][CH:33]([CH3:35])[CH3:34])[CH:29]([CH3:30])[CH3:31])(=[O:38])[CH3:37]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 103230822-[(1R, 2S)-2-{(S)-2-cyclohexylmethoxycarbonylamino-4-methylvalerylamino}-1-hydroxy-3-methylbutyl]-3-phenylcyclopropenone

생성물 1

HCID 537714092-[(1R,2S)-1-acetoxy-2-{(S)-2-cyclohexylmethoxycarbonylamino-4-methylvalerylamino}-3-methylbutyl]-3-phenylcyclopropenone수율 45.1%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
2회
HCID 8471Triethylamine용매

실험 절차

To 5 ml of a methylene chloride solution of 149 mg of 2-[(1R,2S)-2-{(S)-2-cyclohexylmethoxycarbonylamino-4-methylvalerylamino}-1-hydroxy-3-methylbutyl]-3-phenylcyclopropenone obtained in Example 2 were added 81 mg of acetyl chloride and 102 mg of triethylamine. The resultant mixture was stirred at room temperature for 3 hours, mixed with diluted hydrochloric acid and shaken with methylene chloride. The organic layer was washed with water, saturated aqueous sodium bicarbonate and saturated brine in that order, dried over magnesium sulfate and filtered. The filtrate was concentrated and chromatographed on a column of silica gel, eluting with hexane:ethyl acetate (1:1) to give 73 mg of the titled product.

후처리

  1. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate and saturated brine in that order
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customchromatographed on a column of silica gel
  6. washeluting with hexane:ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-315bb8053a094bd09852279fad8ef177
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05416117

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