Benzyl 1-(di-tert-butoxyphosphoryloxy)-2-phenylpropan-2-ylcarbamate → 2-Amino-2-phenylpropyl di-tert-butyl phosphate

HRID 605407Notes

Reaction equation

HRID 605407 reaction equation
[C:1]([O:5][P:6]([O:13][CH2:14][C:15]([NH:23]C(=O)OCC1C=CC=CC=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.CO.[OH-].[OH-].[Pd+2]>[P:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])([O:13][CH2:14][C:15]([NH2:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])=[O:7]

Participants

5

Reactant 1

HCID 67041192Benzyl 1-(di-tert-butoxyphosphoryloxy)-2-phenylpropan-2-ylcarbamate

Product 1

HCID 670410332-Amino-2-phenylpropyl di-tert-butyl phosphate

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 442B (0.10 g, 0.21 mmol) and 20% palladium hydroxide on carbon (0.02 g) in ethyl acetate (1 mL) and methanol (1 mL) was stirred under an atmosphere of hydrogen or 18 hours. The reaction was filtered through a bed of celite and concentrated to give the title compound, which was used without further purification (0.073 g).

Workup

  1. filtrationThe reaction was filtered through a bed of celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-63472ec7666845e59d489b56a0fe1ec6
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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