Diisopropylethylamine → tert-butyl(1-(2-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonyl)cyclopropyl)methylcarbamate

HRID 1855187ノート

反応式

HRID 1855187 の反応式
CCN(C(C)C)C(C)C.[NH:10]([C:12]([C:14]1([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:16][CH2:15]1)=[O:13])[NH2:11].[CH2:26]([O:33][N:34]1[C:40](=[O:41])[N:39]2[CH2:42][C@H:35]1[CH2:36][CH2:37][CH:38]2[C:43](O)=[O:44])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:21]([O:20][C:19](=[O:25])[NH:18][CH2:17][C:14]1([C:12]([NH:10][NH:11][C:43]([CH:38]2[CH2:37][CH2:36][C@@H:35]3[CH2:42][N:39]2[C:40](=[O:41])[N:34]3[O:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:44])=[O:13])[CH2:16][CH2:15]1)([CH3:22])([CH3:24])[CH3:23]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66870453(5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acidHCID 89834475Tert-butyl(1-(hydrazinecarbonyl)cyclopropyl)methylcarbamate

生成物 1

HCID 131732351tert-butyl(1-(2-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonyl)cyclopropyl)methylcarbamate収率 85.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

DIPEA (14 g, 0.11 mol) was added to a solution of tert-butyl (1-(hydrazinecarbonyl)cyclopropyl)methylcarbamate (10.0 g, 0.044 mol), (5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (10 g, 0.036 mol), and HATU (15 g, 0.04 mol) in CH2Cl2 (250 mL). The mixture was stirred at rt for 2 hrs. The mixture was diluted with CH2Cl2 (500 mL), washed with H2O (300 mL), dried over Na2SO4, and concentrated. The crude product was washed with EtOAc (200 mL), and filtrated to afford tert-butyl(1-(2-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonyl)cyclopropyl)methylcarbamate (15 g, 85%) as a white solid. ESI-MS (EI+, m/z): 488.3 [M+H]+.

後処理

  1. washwashed with H2O (300 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. washThe crude product was washed with EtOAc (200 mL)
  5. filtrationfiltrated

出典と根拠

ORDレコード
ord-b3269d58c7214b6bbf6b88b5045f046e
出典データセット
uspto-grants-2015_02
特許番号
US08962843B2

反応ノート

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