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

HRID 1976603Notes

Reaction equation

HRID 1976603 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.[CH3:1][O:2][C:3](=[O:26])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1

Participants

4

Reactant 1

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

Product 2

HCID 20668596(E)-Methyl 3-(3,4-difluorophenyl)acrylateHCID 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 piirged with argon, filtered through celite and concentrated in vacuo to give (2R,3S)-3-amino-3-(3,4-difluorophenyl)-2-hydroxypropionic acid methyl ester from trans-3,4-difluorocinnamic 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. filtrationfiltered through celite and
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f70e00d378a746b482b2c46429ed7b91
Source dataset
uspto-grants-2001_05
Patent number
US06228870B1

Reaction notes

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