(S)-2-benzyloxycarbonylamino-4-(t-butyl-dimethyl-silanyloxy)-butyric acid methyl ester → HCID 59464365, compound

HRID 19330Notes

Reaction equation

HRID 19330 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@@H:4]([NH:15]C(OCC1C=CC=CC=1)=O)[CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:26])[C@@H:4]([NH2:15])[CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:12])([CH3:13])[CH3:14])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 67504379(S)-2-benzyloxycarbonylamino-4-(t-butyl-dimethyl-silanyloxy)-butyric acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 59464365HCID 59464365, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a Parr shaker bottle was placed (S)-2-benzyloxycarbonylamino-4-(t-butyl-dimethyl-silanyloxy)-butyric acid methyl ester (478 mg, 1.25 mmol), methanol (10 mL) and 10% palladium on activated carbon (100 mg). The bottle was placed on the Parr Shaker and charged with hydrogen to 40 psi and shaken for 1.5 h. After this time, the mixture was filtered through celite and the filterate concentrated in vacuo to afford (S)-2-amino-4-(t-butyl-dimethyl-silanyloxy)-butyric acid methyl ester (291 mg, 94%) as a colorless oil.

Workup

  1. filtrationAfter this time, the mixture was filtered through celite
  2. concentrationthe filterate concentrated in vacuo

Sources & evidence

ORD record
ord-5d8613283d3c423393a429ea247cb0b2
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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