Sodium Hydroxide → 4-(2-{2-[(2-Tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethoxy)benzoic acid

HRID 914301Notes

Reaction equation

C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][C:13]2[N:14]=[C:15]([S:18][C:19]([CH3:28])([CH3:27])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[S:16][CH:17]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO.O1CCCC1>[C:23]([O:22][C:20](=[O:21])[C:19]([S:18][C:15]1[S:16][CH:17]=[C:13]([CH2:12][CH2:11][O:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:29])=[O:2])=[CH:9][CH:8]=2)[N:14]=1)([CH3:28])[CH3:27])([CH3:24])([CH3:25])[CH3:26]

Participants

Conditions

Temperature: 60 °C

Procedure

4-(2-{2-[(2-tert-Butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethoxy)benzoic acid methyl ester (7.0 g) obtained in Example 60-1 was dissolved in methanol (50 mL) and tetrahydrofuran (30 mL), 1 mol/L aqueous sodium hydroxide solution (24 ml) was added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, aqueous 10% citric acid solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (6.8 g) as a white solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure, aqueous 10% citric acid solution
additionwas added
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-7df8f7dd6ccd40b2ba28df5227c78ad6
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026370B2

Reaction notes

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