Acetic Acid → 2-(1-Benzyl-2-oxo-2,5-dihydro-1h-pyrrol-3-yl)-n-hydroxy-acetamide
Reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[C:6](=[O:17])[N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH:9]=1.CO.[NH2:21][O:22][K].C(O)(=O)C>CO.C(Cl)(Cl)Cl>[CH2:10]([N:7]1[CH2:8][CH:9]=[C:5]([CH2:4][C:3]([NH:21][OH:22])=[O:2])[C:6]1=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
24 mg of (1-benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-acetic acid methyl ester (p) prepared by the above Step 2 was dissolved in methanol solution (0.1 mmol) and then 1.7 M methanolic suspension solution containing NH2OK (0.4 ml, 0.68 mmol) was added thereto at 0° C. and the resulting mixture was stirred for 4 hrs at room temperature. The resulting mixture was neutralized with 0.02 ml of acetic acid, diluted with 10% methanol/chloroform solution, filtered and concentrated in vacuo. The resulting compound was purified by Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1:9) as an eluant to give 12 mg of 2-(1-benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-N-hydroxy-acetamide (q) (yield: 48%).
Workup
- additionwas added
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting compound was purified by Silica gel column chromatography with a solvent mixture
- additionmixed with methanol and chloroform (1:9) as an eluant
Sources & evidence
- ORD record
- ord-e345325c36684cb0b1527cbc2932cd47
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846963B2
Reaction notes
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