Ethyl Acetate → 1-(1,1-Dimethylethyl) hydrogen L-glutamate

HRID 1860284Notes

Reaction equation

HRID 1860284 reaction equation
[C:1]([O:5][C:6](=[O:24])[C@@H:7]([NH:13]C(OCC1C=CC=CC=1)=O)[CH2:8][CH2:9][C:10]([OH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>CO.[Pd]>[C:1]([O:5][C:6](=[O:24])[C@@H:7]([NH2:13])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 6994036Z-Glu-OtBu

Product 1

HCID 1175051-(1,1-Dimethylethyl) hydrogen L-glutamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 25.0 g (74.1 mmol) (S)-2-(benzyloxycarbonylamino)pentanedioic acid 1-tert.-butyl ester (prepared according to Liebigs Ann. Chem. 1961, 646, 127) in 500 ml dry methanol were added 2.5 g 10% Pd/C, and the mixture was stirred over night at room temperature under an atmosphere of hydrogen. The catalyst was removed by filtration through celite and the filtrate was concentrated under reduced pressure. The remaining solid title compound was purified by stirring with a small amount of ethanol, filtered with suction, and dried in vacuo. Another crop (1.7 g) was obtained after concentration of the mother liquid and stirring of the residue with ethyl acetate.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe remaining solid title compound was purified
  4. stirringby stirring with a small amount of ethanol
  5. filtrationfiltered with suction
  6. customdried in vacuo
  7. customAnother crop (1.7 g) was obtained after concentration of the mother liquid

Sources & evidence

ORD record
ord-71008cb35c0747dc90dab36f4ad8ab56
Source dataset
uspto-grants-2003_03
Patent number
US06528534B2

Reaction notes

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