Sodium Hydroxide → HCID 9804149, compound
Reaction equation
[CH:1]1[C:14]2[N:13]([CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:30][CH2:31][CH3:32])[C:26]([O:28]C)=[O:27])=[CH:20][CH:19]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[CH:1]1[C:14]2[N:13]([CH2:15][CH2:16][O:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:24][CH:25]([O:30][CH2:31][CH3:32])[C:26]([OH:28])=[O:27])=[CH:22][CH:23]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of methyl 3-[4-[2-(phenothiazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoate (7.5 g, 16.70 mmol) obtained in example 4 in methanol (50 mL) was added aqueous 10% sodium hydroxide (20 mL). The reaction mixture was stirred at ca. 25° C. for 3h. The solvent was removed under reduced pressure and the residue was acidified with 2 N hydrochloric acid, extracted with ethyl acetate (2×100 mL). The combined ethyl acetate extract was washed with water (50 mL), brine (50 mL), dried (Na2SO4), filtered and solvent was evaporated under reduced pressure. The residue was chromatographed over silica gel using a mixture of dichloromethane and methanol (9:1) as an eluent to afford the title compound (6.0 g, 83%) as a white solid. mp: 79-82° C.
Workup
- customThe solvent was removed under reduced pressure
- extractionextracted with ethyl acetate (2×100 mL)
- extractionThe combined ethyl acetate extract
- washwas washed with water (50 mL), brine (50 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customsolvent was evaporated under reduced pressure
- customThe residue was chromatographed over silica gel using
- additiona mixture of dichloromethane and methanol (9:1) as an eluent
Sources & evidence
- ORD record
- ord-81765fe649314a1988e389840009dccf
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06054453
Reaction notes
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