Hydrazine → tert-butyl N-((1S)-1-(hydrazinecarbonyl)ethyl)carbamate

HRID 1850132Notes

Reaction equation

HRID 1850132 reaction equation
[NH2:1][NH2:2].[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH3:16])[C:12](OC)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>>[NH:1]([C:12](=[O:13])[C@@H:11]([NH:10][C:8](=[O:9])[O:7][C:3]([CH3:6])([CH3:5])[CH3:4])[CH3:16])[NH2:2]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 10856577Boc-L-alanine methyl ester

Product 1

HCID 10241974tert-butyl N-((1S)-1-(hydrazinecarbonyl)ethyl)carbamateYield 88.7%

Conditions

Temperature
72 °C

Procedure

A solution of hydrazine (234 mg, 7.31 mmol, 1.5 equv. in 8 ml of THF) was added to (S)-methyl 2-(tert-butoxycarbonylamino)propanoate (1000 mg, 4.88 mmol, 1.0 equv.), it was stirred in a sealed tube and refluxed (72° C.) overnight (18 hours), the solvent was removed to yield the desired product (880 mg, white solid) in 84% yield.

Workup

  1. customthe solvent was removed

Sources & evidence

ORD record
ord-fda35eb829924fd1a8414ffaa95e0797
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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