Methyl 2-[[[(phenylmethoxy)carbonyl]amino]methyl]-4-oxazolecarboxylate → 2-Aminomethyloxazole-4-carboxylic acid methyl ester

HRID 1437142Notes

Reaction equation

HRID 1437142 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:10][NH:11]C(OCC2C=CC=CC=2)=O)[O:8][CH:9]=1)=[O:4]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:10][NH2:11])[O:8][CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 69063652Methyl 2-[[[(phenylmethoxy)carbonyl]amino]methyl]-4-oxazolecarboxylate

Product 1

HCID 99894612-Aminomethyloxazole-4-carboxylic acid methyl esterYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

2-(Benzyloxycarbonylaminomethyl)oxazole-4-carboxylic acid methyl ester (0.439 g) (prepared as described in; Journal of Peptide Science (1999), 5(9), 392-398) was dissolved in ethyl acetate (13 ml) and hydrogenated with vigorous stirring at 20° C. and 1 atmosphere of pressure using 10% palladium on carbon catalyst (0.20 g) for 4 hours. The mixture was filtered using celite filter aid and the solvent evaporated from the filtrate in vacuo to give the title compound as a yellow solid (0.197 g)

Workup

  1. customfor 4 hours
  2. filtrationThe mixture was filtered
  3. filtrationfilter aid
  4. customthe solvent evaporated from the filtrate in vacuo

Sources & evidence

ORD record
ord-7822186b5dfe43ab8be5c88d7d8ae696
Source dataset
uspto-grants-2009_11
Patent number
US07622464B2

Reaction notes

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