Acetic Acid → 3-(1-Benzyl-2-oxo-2,5,6,7-tetrahydro-1h-azepin-3-yl)-n-hydroxy-propionamide
Reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[C:7](=[O:20])[N:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:10][CH2:11][CH:12]=1.CO.[NH2:24][O:25][K].C(O)(=O)C>C(OCC)(=O)C>[CH2:13]([N:8]1[CH2:9][CH2:10][CH2:11][CH:12]=[C:6]([CH2:5][CH2:4][C:3]([NH:24][OH:25])=[O:2])[C:7]1=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
108 mg of compound (d) prepared by the above Step 3 was dissolved in methanol solution (0.376 mmol) and then 1.7 M methanolic suspension solution containing NH2OK (1.315 ml, 2.63 mmol) was added thereto at 0° C. and the resulting mixture was stirred for 3 hrs at room temperature. The resulting mixture was neutralized with 0.02 ml of acetic acid, diluted with 10 ml of ethyl acetate solution, filtered and concentrated in vacuo. The resulting compound was purified by column chromatography on Silica gel with methanol/chloroform (1:10) solvent mixture as an eluant to give 46 mg of the title compound (e1) (yield: 43%).
Workup
- additionwas added
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting compound was purified by column chromatography on Silica gel with methanol/chloroform (1:10) solvent mixture as an eluant
Sources & evidence
- ORD record
- ord-1ff50168c45043a893448831e28cf43d
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723376B2
Reaction notes
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