(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 1383782Notes

Reaction equation

HRID 1383782 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 esterYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2R, 3S)-N-benzyloxycarbonyl-3-amino-3-(3,4-diflurophenyl)-2-hydroxypropionic acid methyl ester (>12.2 g, 33.3 mmol maximum) was dissolved in 750 mL ethanol. The flask was purged and filled with argon three times. Palladium on carbon (2 g, 10% wt) was added under argon and the suspension was again purged and filled with argon three times. The suspension was then purged, filled with hydrogen, and stirred 16 h. The suspension was purged, filled with argon three times, filtered through celite and concentrated in vacuo to give (2R, 3S)-3-amino-3-(3,4-difluorophenyl)-2-hydroxypropionic acid methyl ester (5.8 g, 25 mmol, 75% from trans-3,4-difluorocinnamic acid methyl ester).

Workup

  1. customThe flask was purged
  2. additionfilled with argon three times
  3. additionPalladium on carbon (2 g, 10% wt) was added under argon
  4. customthe suspension was again purged
  5. additionfilled with argon three times
  6. customThe suspension was then purged
  7. additionfilled with hydrogen
  8. customThe suspension was purged
  9. additionfilled with argon three times
  10. filtrationfiltered through celite and
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d70c839dcd674d44b65170ace2f5f225
Source dataset
uspto-grants-2001_07
Patent number
US06255315B1

Reaction notes

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