Methyl 4-[bis(tert-Butoxy)phosphoryl-fluoromethyl]-N-(benzyloxycarbonyl)-D,L-phenylalaninate → Methyl 4-[bis(tert-Butoxy)phosphoryl-fluoromethyl]-D,L-phenylalaninate

HRID 258174Notes

Reaction equation

HRID 258174 reaction equation
[C:1]([O:5][P:6]([CH:13]([F:37])[C:14]1[CH:36]=[CH:35][C:17]([CH2:18][CH:19]([C:31]([O:33][CH3:34])=[O:32])[NH:20]C(OCC2C=CC=CC=2)=O)=[CH:16][CH:15]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:9]([O:8][P:6]([CH:13]([F:37])[C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH:19]([C:31]([O:33][CH3:34])=[O:32])[NH2:20])=[CH:35][CH:36]=1)([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])([CH3:10])([CH3:11])[CH3:12]

Participants

4

Reactant 1

HCID 10369964Methyl 4-[bis(tert-Butoxy)phosphoryl-fluoromethyl]-N-(benzyloxycarbonyl)-D,L-phenylalaninate

Product 1

HCID 10250578Methyl 4-[bis(tert-Butoxy)phosphoryl-fluoromethyl]-D,L-phenylalaninateYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 20 (1.09 g, 2.03 mmol) in anhydrous MeOH (50 mL) is hydrogenated over 10% Pd.C (436 mg) under H2 (45 psi) in a Parr apparatus. The vessel is evacuated and replenished with H2 at approximately 30 minute intervals. After 4 hours, the mixture is removed, filtered through celite and solvent removed under reduced pressure, yielding crude 21 (813 mg). Purification by silica gel chromatography affords pure 21 (694 mg, 85%).

Workup

  1. customThe vessel is evacuated
  2. waitAfter 4 hours
  3. customthe mixture is removed
  4. filtrationfiltered through celite and solvent
  5. customremoved under reduced pressure

Sources & evidence

ORD record
ord-e9f3f2d0c5634a6e911ce95d0b38c44c
Source dataset
uspto-grants-1993_11
Patent number
US05264607

Reaction notes

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