Acetic Acid → 3-Benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1-(2-oxo-ethyl)-1,4-dihydro-pyridine-2-carboxylic acid methyl ester
Reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:32])[C:12]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:13]3[C:18](=[O:19])N(CCC)C=C[N:14]3[CH:23]=2)=[O:9])=[CH:4][CH:3]=1.[C:35]([OH:38])(=[O:37])[CH3:36].Cl[CH2:40]Cl>>[CH3:40][O:37][C:35]([C:36]1[N:14]([CH2:13][CH:18]=[O:19])[CH:23]=[C:10]([C:8](=[O:9])[NH:7][CH2:6][C:5]2[CH:33]=[CH:34][C:2]([F:1])=[CH:3][CH:4]=2)[C:11](=[O:32])[C:12]=1[O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:38]Participants
Procedure
According to the method of synthesizing a compound 17-1, the crude purified product (503 mg) of a compound 48 was obtained at a yield of 82% from a compound 16 (600 mg), 2) To a solution of a compound 48 (100 mg, 0.22 mmol), isobutylaldehyde (39 μl, 0.432 mmol) and acetic acid (25 μl, 0.432 mmol) in dichloromethane (4 ml) was added sodium triacetoxyborohydride (92 mg, 0.432 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. Further, isobutylaldehyde (200 and sodium triacetoxyborohydride (46 mg) were added, and the mixture was stirred for 30 minutes. To the reaction solution was added water, this was extracted with chloroform, and the organic layer was washed with an aqueous saturated sodium bicarbonate solution. After drying, the solvent was distilled off under reduced pressure, and this was purified by silica gel column chromatography. A compound 49 (87 mg) was obtained as a colorless crystal at a yield of 78%.
Workup
- customthe crude purified product (503 mg) of a compound 48
Sources & evidence
- ORD record
- ord-55c5a5d5477f48628217092007e4746a
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778943B2
Reaction notes
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