HCID 25729991, compound → HCID 15342932, compound

HRID 1006404Notes

Reaction equation

HRID 1006404 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:26])[C@H:7]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:8]C(OCC1C=CC=CC=1)=O.[H][H]>C(O)C.[Pd].C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:26])[C@H:7]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[NH2:8]

Participants

6

Reactant 2

HCID 25729991HCID 25729991, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15342932HCID 15342932, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(carbobenzyloxy)-L-phenylalanine 2-methoxy-ethyl ester (4.4 g, 12.3 mmol) in ethanol (75 mL) was treated with palladium on charcoal catalyst (440 mg, 10% Pd on charcoal) as a slurry in ethyl acetate (10 mL). Hydrogen gas was passed through the suspension for 3 hours. The reaction mixture was filtered and concentrated under reduced pressure to provide L-phenylalanine 2-methoxy-ethyl ester as a colourless oil (2.5 g, 92%). 1H-NMR; d (methanol-d4), 7.35-7.20 (5H, m), 4.27 (2H, m), 3.79 (1H, m), 3.57 (2H, m), 3.38 (3H, s), 3.10 (1H, dd), 2.90 (1H, dd) and 1.64 (2H, s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-113cc00a68da48ebbfea6d93a93ce49b
Source dataset
uspto-grants-2004_09
Patent number
US06790834B1

Reaction notes

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