Pyridine → (+/-)-Phenylmethyl-[1-(acetyloxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate
Reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:22])[NH:10][CH:11]([CH2:20][OH:21])[C:12](=[O:19])[NH:13][N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].N1C=CC=CC=1>ClCCl.CN(C)C=O>[C:1]1([CH2:7][O:8][C:9](=[O:22])[NH:10][CH:11]([CH2:20][O:21][C:23](=[O:25])[CH3:24])[C:12](=[O:19])[NH:13][N:14]2[CH:15]=[CH:16][CH:17]=[CH:18]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of (±)-phenylmethyl-[1-(hydroxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate (4.26 g) in 100 ml of dichloromethane and 20 ml of dimethylformamide were added acetic anhydride (3.0 ml) and pyridine (2.5 ml). The reaction mixture was stirred overnight at room temperature and then combined with the product from a 5.41 mmol scale reaction which was performed under the same conditions. The reaction mixture was washed with 5% citric acid and water, and dried over magnesium sulfate. After evaporation, the crude product was purified by flash column chromatography (silica gel, DCM/methanol, 30:1). Recrystallization from ethyl acetate/n-hexane afforded the product as a powder (2.96 g, 44%), m.p. 154°-155° C.
Workup
- customcombined with the product from a 5.41 mmol scale reaction which
- washThe reaction mixture was washed with 5% citric acid and water
- dry with materialdried over magnesium sulfate
- customAfter evaporation
- customthe crude product was purified by flash column chromatography (silica gel, DCM/methanol, 30:1)
- customRecrystallization from ethyl acetate/n-hexane
Sources & evidence
- ORD record
- ord-983234081bb64342ab3ec32a214a0748
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05274116
Reaction notes
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