Hydrochloric Acid → 2-[5-chloro-2-[2-(1-naphthyl)propanoylamino]phenylmethyl]Benzoic Acid
Reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[NH:18][C:19](=[O:32])[CH:20]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[CH3:21].[OH-].[Na+].Cl>>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]([NH:18][C:19](=[O:32])[CH:20]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[CH3:21])=[C:11]([CH2:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:33])=[O:2])[CH:16]=1Participants
4
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 2-[5-chloro-2-[2-(1-naphthyl)propanoylamino]phenyl methyl]benzoic acid methyl ester (440 mg; prepared in Example 1.) in methanol-dioxane (1:1; 8 ml) was added 2 mol/L aqueous solution of sodium hydroxide (3 ml) and the mixture was stirred for 3 hours at 50° C. The solution was acidified with hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried and concentrated to give a crude crystal. It was washed with ethyl acetate-hexane to give the title compound (342 mg; white powder) having the following physical data.
Workup
- extractionwas extracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materiala saturated aqueous solution of sodium chloride, dried
- concentrationconcentrated
- customto give a crude crystal
- washIt was washed with ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-8fb7c53be312416295a6f9e6b7c1af69
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196198B2
Reaction notes
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