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

HRID 2246596ノート

反応式

HRID 2246596 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-98beebfac0dc4887a2692e7f3d56f6d1
出典データセット
uspto-grants-2010_03
特許番号
US07687508B2

反応ノート

読み込み中…