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

HRID 57404Notes

Reaction equation

HRID 57404 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:14])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:15][NH2:16]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH3:14])[C:10]([NH:15][NH2:16])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9321Hydrazine2×HCID 10856577Boc-L-alanine methyl ester

Product 1

HCID 10241974tert-butyl N-((1S)-1-(hydrazinecarbonyl)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-methyl 2-((tert-butoxycarbonyl)amino)propanoate (1.00 g, 4.92 mmol) and hydrazine (0.23 mL, 1.5 equiv) in THF (8 mL) was heated in a sealed tube at 72° C. for 15 hours. Additional hydrazine (0.23 mL, 1.5 equiv) was added and heating was continued for another 21 hours. The reaction was then cooled to room temperature and concentrated in vacuo to give crude (S)-tert-butyl(1-hydrazinyl-1-oxopropan-2-yl)carbamate (1 g, white solid), which was used without purification. 1H NMR (400 MHz, CDCl3) δ 4.20 (m, 1H), 1.44 (s, 9H), 1.36 (d, J=7.1 Hz, 3H).

Workup

  1. temperatureheating
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af3f2e06c332425aab8953dc44bfeb70
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

Loading…