Sodium Hydroxide → HCID 9804149, compound

HRID 396933Notes

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]=1

Participants

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 3 h. 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-4db9e20f1baa4e5fad048ac4da3f2d7e
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608194B1

Reaction notes

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