Water → 3-(5-(3-Chloro-2-fluorobenzyl)-2-fluoro-4-methoxyphenyl)-3-oxopropionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH:5]([C:9](=[O:28])[C:10]1[CH:15]=[C:14]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[F:24])[C:13]([O:25][CH3:26])=[CH:12][C:11]=1[F:27])C(=O)C)[CH3:2].O.C([O-])(=O)C.[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:9]([C:10]1[CH:15]=[C:14]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[F:24])[C:13]([O:25][CH3:26])=[CH:12][C:11]=1[F:27])=[O:28])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-(5-(3-chloro-2-fluorobenzyl)-2-fluoro-4-methoxybenzoyl)-3-oxobutyric acid ethyl ester prepared in Step VI-1 in ethanol were successively added water (5 ml) and sodium acetate (7.87 g) with stirring at room temperature, and the mixture was stirred for 4 days. Water (20 ml) was added to the reaction suspension at 70° C. and, after confirmation of dissolution, the mixture was cooled to room temperature. A seed crystal (10 mg) of the title compound was added and, after stirring for 1 hr, water (75 ml) was added again, and the mixture was stirred for 4 hr. The precipitated crystals were collected by filtration, washed with 50% ethanol (20 ml) and vacuum dried to give 3-(5-(3-chloro-2-fluorobenzyl)-2-fluoro-4-methoxyphenyl)-3-oxopropionic acid ethyl ester (10.3 g, yield 84.5%). This was identified as the title compound by HPLC.
Workup
- stirringthe mixture was stirred for 4 days
- dissolutionafter confirmation of dissolution
- temperaturethe mixture was cooled to room temperature
Sources & evidence
- ORD record
- ord-98e9e3ec32d246ffaced561c63ee49ca
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383819B2
Reaction notes
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