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

HRID 1427652Notes

Reaction equation

HRID 1427652 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-d2b68b9ef8e649ca925dd68d5b7d1b2f
Source dataset
uspto-grants-2015_01
Patent number
US08933233B2

Reaction notes

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