(+/-)-Phenylmethyl-[1-(acetyloxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate → (+/-)-3-(Acetyloxy)-2-amino-N-1H-pyrrol-1-ylpropanamide
Reaction equation
C1(COC(=O)[NH:10][CH:11]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C:12](=[O:19])[NH:13][N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)C=CC=CC=1>CO.[Pd]>[C:22]([O:21][CH2:20][CH:11]([NH2:10])[C:12]([NH:13][N:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1)=[O:19])(=[O:24])[CH3:23]Participants
4
Procedure
(±)-Phenylmethyl-[1-(acetyloxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate (4.18 g) was dissolved in 100 ml of methanol and 5% Pd/C (450 mg) was added. The solution was hydrogenated at atmospheric pressure and room temperature until absorption of 90% of the theoretical amount of hydrogen. The catalyst was removed by filtration and the filtrate was evaporated to dryness. The residue was purified by flash column chromatography (silica gel, ethyl acetate/methanol, 19:1) and the desired fractions combined and evaporated. Recrystallization of the residue from ethyl acetate/methanol/hexane afforded the product obtained as a powder (1.24 g), m.p. 147°-148° C.
Workup
- customThe solution was hydrogenated at atmospheric pressure and room temperature until absorption of 90% of the theoretical amount of hydrogen
- customThe catalyst was removed by filtration
- customthe filtrate was evaporated to dryness
- customThe residue was purified by flash column chromatography (silica gel, ethyl acetate/methanol, 19:1)
- customevaporated
- customRecrystallization of the residue from ethyl acetate/methanol/hexane
- customafforded the product
Sources & evidence
- ORD record
- ord-00ace85348c145e8a0111b693bafdd62
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05580987
Reaction notes
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