Hydrochloric Acid → (E)-3-[6-[[3,5-Bis(trimethylsilyl)benzoyl]amino]-pyridin-3-yl]acrylic acid
Reaction equation
[CH3:1][Si:2]([CH3:30])([CH3:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19]CC)=[O:18])=[CH:11][CH:10]=1)=[O:7].[OH-].[Na+].Cl>C(O)C>[CH3:30][Si:2]([CH3:1])([CH3:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)=[O:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Compound 1b (232 mg) was dissolved in ethanol (7.89 ml). A 2N sodium hydroxide aqueous solution (5.26 ml) was added thereto and the mixture was stirred at room temperature overnight. The reaction mixture was ice-cooled, and a 2N hydrochloric acid aqueous solution (5.26 ml) was added to neutralize the mixture. Then the solvent was distilled off. The reaction mixture was ice-cooled, and a 2N hydrochloric acid aqueous solution (0.5 ml) was added to adjust the pH of the mixture to 1. The mixture was stirred for 1 hour. The precipitated solid was filtered off and vacuum-dried to give Compound 1 (88.0 mg, 41%) as a white solid.
Workup
- temperaturecooled
- distillationThen the solvent was distilled off
- temperaturecooled
- additiona 2N hydrochloric acid aqueous solution (0.5 ml) was added
- stirringThe mixture was stirred for 1 hour
- filtrationThe precipitated solid was filtered off
- customvacuum-dried
Sources & evidence
- ORD record
- ord-be65e00901654df79e4a3324fcca969c
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855300B2
Reaction notes
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