(2S,3S)-2-tert-butoxycarbonylamino-3-(2-nitro-phenylamino)-butyric acid → (2S,3S)-3-(2-amino-phenylamino)-2-tert-butoxycarbonylamino-butyric acid

HRID 1486032Notes

Reaction equation

HRID 1486032 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-])=O)[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][C@@H:13]([CH3:14])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([OH:12])=[O:11]

Participants

3

Reactant 1

HCID 90079360(2S,3S)-2-tert-butoxycarbonylamino-3-(2-nitro-phenylamino)-butyric acid

Product 1

HCID 90079354(2S,3S)-3-(2-amino-phenylamino)-2-tert-butoxycarbonylamino-butyric acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask containing a solution of (2S,3S)-2-tert-butoxycarbonylamino-3-(2-nitro-phenylamino)-butyric acid (5.8 g, 17.1 mmol) in ethanol (60 ml) was purged with nitrogen followed by the addition of 10% palladium on carbon (600 mg). The atmosphere above the ethanol solution was exchanged for hydrogen and the reaction mixture stirred vigorously for 30 minutes at atmospheric pressure. The reaction mixture was filtered through a pad of celite and concentrated in vacuo to give (2S,3S)-3-(2-amino-phenylamino)-2-tert-butoxycarbonylamino-butyric acid which was used in the subsequent step without further purification (5.29 g, 100%).

Workup

  1. customwas purged with nitrogen
  2. additionfollowed by the addition of 10% palladium on carbon (600 mg)
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d702a625b49542bca019178badd03b65
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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