(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 1637095Notes

Reaction equation

HRID 1637095 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-difluorophenyl)-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-9b678ccef613423f84f909cedd45048f
Source dataset
uspto-grants-2000_03
Patent number
US06037354

Reaction notes

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