(2S,3S)-benzyl 3-azido-2-(tert-butoxycarbonylamino)butanoate → (2S,3S)-3-Amino-2-((tert-butoxycarbonyl)amino)butanoic acid

HRID 1486081Notes

Reaction equation

HRID 1486081 reaction equation
[N:1]([C@@H:4]([CH3:24])[C@H:5]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:6]([O:8]CC1C=CC=CC=1)=[O:7])=[N+]=[N-]>CO>[NH2:1][C@@H:4]([CH3:24])[C@H:5]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 131736777(2S,3S)-benzyl 3-azido-2-(tert-butoxycarbonylamino)butanoate

Product 1

HCID 90079392(2S,3S)-3-Amino-2-((tert-butoxycarbonyl)amino)butanoic acidYield 103.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2S,3S)-benzyl 3-azido-2-(tert-butoxycarbonylamino)butanoate (1.7 g, 5.08 mmol) and PdC (5%, wet) (340 mg, 319 μmol) in MeOH (16.4 g, 20.7 ml) was shaken under H2 (50 PSI) for 3.5 h, then filtered through a bed of celite and concentrated to give (2S,3S)-3-amino-2-(tert-butoxycarbonylamino)butanoic acid (1.15 g, quant.) as a white solid.

Workup

  1. filtrationfiltered through a bed of celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e1e61d9039044f85929c4381d359301f
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

Loading…