Trifluoroacetic acid → Carbamic acid, [4-(1-hydroxy-1-methylethyl)-2-thiazolyl]-

HRID 32845Notes

Reaction equation

C([O:5][C:6](=[O:17])[NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13]([OH:16])([CH3:15])[CH3:14])[N:12]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[OH:16][C:13]([C:11]1[N:12]=[C:8]([NH:7][C:6](=[O:5])[OH:17])[S:9][CH:10]=1)([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

[4-(1-Hydroxy-1-methyl-ethyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (250 mg, 0.92 mmol) was taken into dry dichloromethane and cooled in an ice bath. To this was added trifluoroacetic acid and the mixture stirred at 0° C. for 4 hours. The mixture was evaporated and the residue partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was separated out and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate and evaporated. Chromatography of the residue over silica gel gradient eluted with 1:99 up to 3:97 methanol in dichloromethane gave [4-(1-hydroxy-1-methyl-ethyl)-thiazol-2-yl]-carbamic acid (56 mg, 39%) as a white solid.

Workup

temperaturecooled in an ice bath
customThe mixture was evaporated
customthe residue partitioned between dichloromethane and saturated aqueous sodium bicarbonate
customThe organic layer was separated out
extractionthe aqueous layer was extracted with dichloromethane
dry with materialThe combined organic extracts were dried over sodium sulfate
customevaporated
washChromatography of the residue over silica gel gradient eluted with 1:99 up to 3:97 methanol in dichloromethane

Sources & evidence

ORD record: ord-2e1598615e28476795a377513046e112
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427635B2

Reaction notes

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