Hydrazine hydrate (1:1) → Tert-butyl(1-(hydrazinecarbonyl)cyclopropyl)methylcarbamate

HRID 1427652ノート

反応式

HRID 1427652 の反応式
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]([O:17][C:18]([NH:20][CH2:21][C:22]1([C:25]([OH:27])=O)[CH2:24][CH2:23]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[NH2:28][NH2:29].O>C1COCC1>[C:13]([O:17][C:18](=[O:19])[NH:20][CH2:21][C:22]1([C:25]([NH:28][NH2:29])=[O:27])[CH2:24][CH2:23]1)([CH3:16])([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 24654Hydrazine hydrate (1:1)HCID 682631,1'-CarbonyldiimidazoleHCID 51340346Boc-amcp-OH

生成物 1

HCID 89834475Tert-butyl(1-(hydrazinecarbonyl)cyclopropyl)methylcarbamate収率 84.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

CDI (12.5 g, 0.077 mol) was added to a 0° C. solution of 1-((tert-butoxycarbonylamino)methyl)cyclopropanecarboxylic acid (15.0 g, 0.07 mol) in THF (250 mL). The mixture was allowed to warm to rt, and stirred at rt. for 2 hrs, and then NH2NH2.H2O (10.5 g, 0.21 mol) was added rapidly. The mixture was stirred for another 1 hr. The reaction mixture was concentrated, and then CH2Cl2 (500 mL) was added. The combined organic layer was washed with H2O (100 mL), dried over Na2SO4, and concentrated to afford tert-butyl(1-(hydrazinecarbonyl)cyclopropyl)methylcarbamate (13.5 g, 84%). ESI-MS (EI+, m/z): 230.2 [M+H]+.

後処理

  1. stirringThe mixture was stirred for another 1 hr
  2. concentrationThe reaction mixture was concentrated
  3. additionCH2Cl2 (500 mL) was added
  4. washThe combined organic layer was washed with H2O (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d2b68b9ef8e649ca925dd68d5b7d1b2f
出典データセット
uspto-grants-2015_01
特許番号
US08933233B2

反応ノート

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