(S)-2-(tert-butoxycarbonylamino)-3-(5-methyl-2-nitrophenoxy)propanoic acid → (S)-3-(2-amino-5-methylphenoxy)-2-(tert-butoxycarbonylamino)propanoic acid

HRID 1055370Notes

Reaction equation

HRID 1055370 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-])=O)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:22][C:16]1[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=1[O:14][CH2:13][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 67076916(S)-2-(tert-butoxycarbonylamino)-3-(5-methyl-2-nitrophenoxy)propanoic acid

Product 1

HCID 67076885(S)-3-(2-amino-5-methylphenoxy)-2-(tert-butoxycarbonylamino)propanoic acidYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-2-(tert-butoxycarbonylamino)-3-(5-methyl-2-nitrophenoxy)propanoic acid (7.50 g, 22.0 mmol, Eq: 1.00) and 10% Pd/C (0.75 g, Eq: 0.03) in MeOH (300 mL) were hydrogenated at ambient pressure for 4 h at RT. The mixture was filtered through a pad of silica gel and the filtrate was concentrated to give (S)-3-(2-amino-5-methylphenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (3.85, 56%) as a yellow solid which was used without purification.

Workup

  1. filtrationThe mixture was filtered through a pad of silica gel
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7554857a1739438f9d3a8be82a4c7925
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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