Citric Acid → 4-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid

HRID 914361Notes

Reaction equation

C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([S:27][C:28]([CH3:36])([CH3:35])[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])[S:25][CH:26]=2)[C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][N:13]=2)=[CH:6][CH:5]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[C:31]([C:29](=[O:30])[C:28]([S:27][C:24]1[S:25][CH:26]=[C:22]([CH2:21][CH2:20][N:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=2)[C:12]2[N:13]=[CH:14][C:15]([CH2:18][CH3:19])=[CH:16][N:17]=2)[N:23]=1)([CH3:35])[CH3:36])([CH3:32])([CH3:33])[CH3:34]

Participants

Conditions

Temperature: 60 °C

Procedure

4-{[(2-{2-[(2-tert-Butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid methyl ester (2.2 g) synthesized in Example 437-1 was dissolved in methanol (50 mL) and tetrahydrofuran (50 mL), 1N aqueous sodium hydroxide solution (16 ml) was added, and the mixture was stirred at 60° C. for 4 hr. Aqueous 10% citric acid solution was added, and the mixture was extracted with chloroform. The insoluble material was filtered off, and the filtrate was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.0 g) as an oil.

Workup

extractionthe mixture was extracted with chloroform
filtrationThe insoluble material was filtered off
washthe filtrate was washed with water
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-b2741d158073431cb141bd49fed25898
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026370B2

Reaction notes

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