(2S,3S)-2-tert-butoxycarbonylamino-3-(5-methyl-2-nitro-phenoxy)-butyric acid → (2S,3S)-3-(2-amino-5-methyl-phenoxy)-2-tert-butoxycarbonylamino-butyric acid

HRID 1055374Notes

Reaction equation

HRID 1055374 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:13]([O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[N+:23]([O-])=O)[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[NH2:23][C:17]1[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=1[O:15][C@@H:13]([CH3:14])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 90036984(2S,3S)-2-tert-butoxycarbonylamino-3-(5-methyl-2-nitro-phenoxy)-butyric acid

Product 1

HCID 90037055(2S,3S)-3-(2-amino-5-methyl-phenoxy)-2-tert-butoxycarbonylamino-butyric acidYield 34%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

(2S,3S)-2-tert-butoxycarbonylamino-3-(5-methyl-2-nitro-phenoxy)-butyri c acid (0.95 g, 2.68 mmol, Eq: 1.00) and 5% Pd/C (200 mg, 94.0 μmol, Eq: 0.0351) in EtOH (100 mL) were hydrogenated overnight at RT and ambient pressure and an additional portion of 10% Pd/C (100 mg, 47.0 μmol, Eq: 0.0176) was added. After 2 h the mixture was filtered through Celite, the filtrate was concentrated and the residue was purified by silica gel chromatography to afford (2S,3S)-3-(2-amino-5-methyl-phenoxy)-2-tert-butoxycarbonylamino-butyric acid (294 mg, 34%) as a solid.

Workup

  1. filtrationAfter 2 h the mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7347c1e7673949d4a407544274bd2e8f
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

Loading…