Water → HCID 68992203, compound

Participants

Reaction Steps

To a 250 mL round-bottomed flask was added sodium chlorite (3.68 g, 40.7 mmol), tert-butyl 4-bromo-5-formylthiazol-2-ylcarbamate (1.18 g, 3.84 mmol), isobutanol (76.8 mL, 3.84 mmol), and an aqueous (30.00 mL, 3.84 mmol) solution of sodium dihydrogen phosphate (3.60 g, 30.0 mmol) followed by 2-methyl-2-butene (4.47 mL, 42.3 mmol). The mixture was stirred vigorously for about 3 hours. LCMS indicated complete conversion to product so the mixture was diluted with water (60 mL) and 120 mL of 1:1 EtOAc/hexanes. The aqueous layer was extracted with 1:1 EtOAc/hexanes, and the combined organic layers were washed with brine, dried over sodium sulfate, and filtered. The solvent was reduced providing the semi-crude product 4-bromo-2-(tert-butoxycarbonyl)thiazole-5-carboxylic acid (1.35 g, 109% yield). The crude product was used immediately without further purification.

Provenance & Evidence