HCID 67077060, compound → HCID 67076712, compound

HRID 1055484Notes

Reaction equation

HRID 1055484 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][C:15]1[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[CH:17][C:16]=1[F:24])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([F:24])[C:15]=1[O:14][CH2:13][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 67077060HCID 67077060, compound

Product 1

HCID 67076712HCID 67076712, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-2-(tert-butoxycarbonylamino)-3-(2-fluoro-6-nitrophenoxy)propanoic acid (2.94 g, 8.54 mmol) and 10% Pd/C (150 mg) in MeOH was stirred under H2 for 4 h. The mixture was filtered through Celite and the cake was washed with MeOH. The filtrate was concentrated to afford (S)-3-(2-amino-6-fluorophenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (2.6 g, 97%) which was used without purification.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe cake was washed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8702e430d64f4f34bbb611636dc87a28
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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