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Bromoacetonitrile → 2-(Trimethylsilyl)ethyl(1r,2s,5r)-2-((s)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(cyanomethylamino)cyclohexylcarbamate

HRID 1866104
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HRID 1866104 반응식
[NH2:1][C@H:2]1[CH2:7][C@@H:6]([NH:8][C:9](=[O:17])[O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C@@H:5]([N:18]2[CH2:22][CH2:21][C@H:20]([NH:23][C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[C:19]2=[O:34])[CH2:4][CH2:3]1.[CH:35]([N:38](C(C)C)CC)(C)[CH3:36].BrCC#N>C(#N)C>[CH2:27]([O:26][C:24]([NH:23][C@H:20]1[CH2:21][CH2:22][N:18]([C@H:5]2[CH2:4][CH2:3][C@@H:2]([NH:1][CH2:36][C:35]#[N:38])[CH2:7][C@H:6]2[NH:8][C:9](=[O:17])[O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:19]1=[O:34])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
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참가 물질

5

반응물 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 866181592-(trimethylsilyl)ethyl (1R,2S,5R)-5-amino-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)cyclohexylcarbamate

생성물 1

HCID 1317278182-(Trimethylsilyl)ethyl(1r,2s,5r)-2-((s)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(cyanomethylamino)cyclohexylcarbamate

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

Example 1, Alternative Preparation, Step 3: A stirring solution of 2-(trimethylsilyl)ethyl (1R,2S,5R)-5-amino-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)cyclohexylcarbamate (400 mg, 0.82 mmol) in acetonitrile (3 mL) was charged sequentially with diisopropylethylamine (315.8 mg, 3 eq) and bromoacetonitrile (109.5 mg, 1.1 eq). The mixture was stirred at40° C. for 30 h. The solvent was removed under reduce pressure. The residue was purified by silica gel column chromatography, using 1.5% of methanol in dichloromethane as the eluant. The desired 2-(trimethylsilyl)ethyl(1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(cyanomethylamino)cyclohexylcarbamate was obtained as a white solid (400 mg, 93%). LC/MS found [M+H]+=530.

후처리

  1. customExample 1, Alternative Preparation, Step 3
  2. customThe solvent was removed
  3. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a6a27017c8e645b3b947e05596f07026
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07629351B2

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