Hydrochloric Acid → HCID 58271197, compound

HRID 1665245Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([F:26])=[CH:21][C:20]=3[O:27][CH3:28])=[CH:15][CH:14]=2)[S:9][CH:10]=1)=[O:5])C.O.[OH-].[Li+].Cl>C1COCC1.O>[F:26][C:22]1[C:23]([F:25])=[CH:24][C:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:8]3[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=3)=[CH:18][CH:17]=2)=[C:20]([O:27][CH3:28])[CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-thiazole-4-carboxylic acid ethyl ester (2.38 g, 5.870 mmol) in THF (40 mL) was treated with a solution of lithium hydroxide monohydrate (2.6 g, 61.96 mmol) in water (40 mL) at room temperature and stirred at 60° C. for 2 h. The mixture was cooled, diluted with water (75 mL), acidified with aq. 3N HCl and extracted with ethyl acetate (3×100 mL). The organic layers were combined, washed with brine (100 mL), dried (MgSO4), filtered and concentrated to 2-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-thiazole-4-carboxylic acid (2.13 g, 96.1%) as a pale yellow solid. LC-MS (ES) calculated for C18H13F2NO4S, 377.37; found m/z 378 [M+H]+.

Workup

temperatureThe mixture was cooled
extractionextracted with ethyl acetate (3×100 mL)
washwashed with brine (100 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated to 2-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-thiazole-4-carboxylic acid (2.13 g, 96.1%) as a pale yellow solid

Sources & evidence

ORD record: ord-89991d27662845238e5bd02c988b8ce7
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039495B2

Reaction notes

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