(2R, 3S)-N-benzyloxycarbonyl-3-amino-3-(3,4-difluorophenyl)-2-hydroxypropionic acid methyl ester → (2R,3S)-3-amino-3-(3,4-difluorophenyl)-2-hydroxypropionic acid methyl ester

HRID 429876Notes

Reaction equation

HRID 429876 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([OH:25])[C@@H:5]([NH:14]C(OCC1C=CC=CC=1)=O)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1>C(O)C>[CH3:1][O:2][C:3](=[O:26])[C@H:4]([OH:25])[C@@H:5]([NH2:14])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1

Participants

3

Reactant 1

HCID 57249284(2R, 3S)-N-benzyloxycarbonyl-3-amino-3-(3,4-difluorophenyl)-2-hydroxypropionic acid methyl ester

Product 1

HCID 57167178(2R,3S)-3-amino-3-(3,4-difluorophenyl)-2-hydroxypropionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2R, 3S)-N-Benzyloxycarbonyl-3-amino-3-(3,4-difluorophenyl)-2-hydroxypropionic acid methyl ester (>12.2 g, 33.3 mmol maximum) was dissolved in 750 mL ethanol. The flask was purged with argon and palladium on carbon (2 g, 10% wt) was added. The suspension was then purged, filled with hydrogen, and stirred 16 h. The suspension was purged with argon, filtered through celite and concentrated in vacuo to give (2R, 3S)-3-amino-3-(3,4-difluorophenyl)-2-hydroxypropionic acid methyl ester.

Workup

  1. customThe flask was purged with argon and palladium on carbon (2 g, 10% wt)
  2. additionwas added
  3. customThe suspension was then purged
  4. additionfilled with hydrogen
  5. customThe suspension was purged with argon
  6. filtrationfiltered through celite and
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca99fa75e42e471391fc07b6b587e118
Source dataset
uspto-grants-2001_11
Patent number
US06319932B1

Reaction notes

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