Chloroform methanol → Methyl 4-[bis(tert-butoxy)phosphorylhydroxymethyl]-D,L-phenylalaninate

HRID 2260001Notes

Reaction equation

HRID 2260001 reaction equation
[N:1]([C:4](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([P:18]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[OH:17])=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[N+]=[N-].[H][H].C(Cl)(Cl)Cl.CO>CO.[Pd]>[C:26]([O:25][P:18]([CH:16]([OH:17])[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[NH2:1])=[CH:11][CH:12]=1)([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])([CH3:27])([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 21584188Chloroform methanolHCID 54085097Methyl alpha-azido-4-[bis(tert-butoxy)phosphorylhydroxymethyl]cinnamateHCID 178418361HCID 178418361, compound

Product 1

HCID 10386317Methyl 4-[bis(tert-butoxy)phosphorylhydroxymethyl]-D,L-phenylalaninateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 7 (1.25 g, 2.85 mmol) in MeOH (50 mL) was hydrogenated in a Parr apparatus over 10% Pd.C (200 mg) under 40 psi H2. The hydrogen was replenished after 10 minutes. The reaction was terminated after 3 hours, and catalyst removed by filtration. Evaporation of solvent yielded 8 as a clear, colorless syrup, 1.17 g (100% crude yield). Silica gel chromatography [CHCl3 :MeOH(25:1)] provided pure 8 (92%).

Workup

  1. customThe reaction was terminated after 3 hours
  2. customcatalyst removed by filtration
  3. customEvaporation of solvent
  4. customyielded 8 as a clear, colorless syrup, 1.17 g (100% crude yield)

Sources & evidence

ORD record
ord-fd9099c15a7c44d68298ca4085c75945
Source dataset
uspto-grants-1995_12
Patent number
US05475129

Reaction notes

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