(S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-6-(trifluoromethyl)phenoxy)propanoic acid → (S)-3-(2-amino-6-(trifluoromethyl)phenoxy)-2-(tert-butoxycarbonylamino)propanoic acid

HRID 1055420Notes

Reaction equation

HRID 1055420 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][C:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][C:16]=1[N+:25]([O-])=O)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:25][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([C:21]([F:22])([F:23])[F:24])[C:15]=1[O:14][CH2:13][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

4

Reactant 1

HCID 90037204(S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-6-(trifluoromethyl)phenoxy)propanoic acid

Product 1

HCID 21091528(S)-3-(2-amino-6-(trifluoromethyl)phenoxy)-2-(tert-butoxycarbonylamino)propanoic acidYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (150 mg) was added to a solution of (S)-2-(tert-butoxycarbonylamino)-3-(2-nitro-6-(trifluoromethyl)phenoxy)propanoic acid (1.5 g, 3.8 mmol) in MeOH and the mixture stirred under H2. After 4 h the mixture was filtered through Celite, the filter cake washed with MeOH and the filtrate concentrated to afford (S)-3-(2-amino-6-(trifluoromethyl)phenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (1.23 g, 89%) which was used without purification.

Workup

  1. filtrationAfter 4 h the mixture was filtered through Celite
  2. washthe filter cake washed with MeOH
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d3cfec6105924a3ea0bae3207d9afde9
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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