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

HRID 1855186노트

반응식

HRID 1855186 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-a22c7f7bc3d74c17b7861722f9cf1158
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962843B2

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