Oxygen → (R)-Methyl 2-acetamidopropanoate

HRID 1585235Notes

Reaction equation

HRID 1585235 reaction equation
[C:1]([NH:4][C:5](=[CH2:10])[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].O=O>CO>[CH3:9][O:8][C:6](=[O:7])[C@@H:5]([CH3:10])[NH:4][C:1](=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 977OxygenHCID 98644Methyl 2-acetamidoacrylate

Product 1

HCID 6951031(R)-Methyl 2-acetamidopropanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-acetamidoacrylate (22 mg, 0.15 mmol) and the catalyst (I) (1 mg, 0.0015, 1 mol %) in degassed methanol (1 ml) was prepared under exclusion of oxygen in a GC-vial. The vial was placed in a 50 ml Parr reactor which was purged with hydrogen and charged to 3.41 MPa (500 psi). After hydrogenation of the mixture overnight, the solvent was evaporated to give the (R)-N-acetylalanine methyl ester (complete conversion, 62.8% ee).

Workup

  1. customwas purged with hydrogen
  2. additioncharged to 3.41 MPa (500 psi)
  3. customAfter hydrogenation of the mixture overnight, the solvent was evaporated

Sources & evidence

ORD record
ord-71eb623e647f485ab24eeb75219c2a86
Source dataset
uspto-grants-1999_08
Patent number
US05936109

Reaction notes

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