(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 1856658Notes

Reaction equation

HRID 1856658 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-0f032e17f94d4f1c9d6171951b5055af
Source dataset
uspto-grants-2000_11
Patent number
US06143750

Reaction notes

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