Ethyl Acetate → (+)-2-Amino-3-(6-methoxy-pyridin-3-yl)-propionic acid methyl ester

HRID 2250217Notes

Reaction equation

HRID 2250217 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]([NH:14]C(OCC1C=CC=CC=1)=O)=[CH:5][C:6]1[CH:7]=[N:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1.C(OCC)(=O)C>[Pd].CO>[CH3:1][O:2][C:3](=[O:25])[CH:4]([NH2:14])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 687043022-Benzyloxycarbonylamino-3-(6-methoxy-pyridin-3-yl)-acrylic acid methyl ester

Product 1

HCID 59639680(+)-2-Amino-3-(6-methoxy-pyridin-3-yl)-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask containing 2-benzyloxycarbonylamino-3-(6-methoxy-pyridin-3-yl)-acrylic acid methyl ester (620 mg), palladium on charcoal (10%, 100 mg), ethyl acetate (10 mL) and methanol (20 mL) was flushed with nitrogen, then hydrogen, before finally affixing a balloon of hydrogen. The reaction was allowed to stir overnight. The flask was flushed with nitrogen, filtered through celite, and concentrated to give 390 mg (quant.) which was used without purification. Mass spec.: 211.11 (MH)+.

Workup

  1. customwas flushed with nitrogen
  2. customThe flask was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customto give 390 mg (quant.) which
  6. customwas used without purification

Sources & evidence

ORD record
ord-d735315dea6d43dfa8bc9665636d01b4
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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