Oxalic Acid → 2-(trimethylsilyl)ethyl (1R,2S)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-oxocyclohexylcarbamate

HRID 2246596노트

반응식

HRID 2246596 반응식
N[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.C(C1C(=O)C(=[O:49])C=C(C(C)(C)C)C=1)(C)(C)C.C1COCC1.C(O)(=O)C(O)=O>CO.O>[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:2](=[O:49])[CH2:7][C@H:6]2[NH:8][C:9](=[O:17])[O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:16])[CH3:15])[C:19]1=[O:34])=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

참가 물질

7

반응물 4

HCID 971Oxalic AcidHCID 8028TetrahydrofuranHCID 769153,5-Di-tert-butyl-1,2-benzoquinoneHCID 866181592-(trimethylsilyl)ethyl (1R,2S,5R)-5-amino-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)cyclohexylcarbamate

생성물 1

HCID 866181582-(trimethylsilyl)ethyl (1R,2S)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-oxocyclohexylcarbamate수율 53.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of 2-(trimethylsilyl)ethyl (1R,2S,5R)-5-amino-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)cyclohexylcarbamate (1.03 g, 2.099 mmol) in methanol (10 ml) was added 3,5-di-tert-butyl-1,2-benzoquinone (0.555 g, 2.52 mmol). This mixture was stirred for 2 hr before THF (6 mL) and water (2 mL) were added along with oxalic acid to pH 4. This mixture was concentrated. The resulting residue was dissolved in ethyl acetate and washed with brine. The organic layer was dried (MgSO4), filtered, and concentrated. This was purified via flash chromatography to give 2-(trimethylsilyl)ethyl (1R,2S)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-oxocyclohexylcarbamate (0.550 g, 1.123 mmol, 53.5% yield). LC/MS found [M+H]+=491.3.

후처리

  1. concentrationThis mixture was concentrated
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis was purified via flash chromatography

출처 및 근거

ORD 기록
ord-98beebfac0dc4887a2692e7f3d56f6d1
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687508B2

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