Triethylamine → 3-{[4-(Methylthio)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

Into a solution of 511 (0.815 g, 4.10 mmol) and dry THF (25.0 mL) was added triethylamine (0.572 mL, 4.10 mmol), followed by a solution of the 508 (0.500 g, 3.42 mmol) dissolved in dry THF (10.0 mL). The reaction was stirred at room temperature. After stirring overnight, the reaction was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed once with water, three times with saturated aqueous. sodium bicarbonate solution, and once with brine. The ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated in vacuo to give crude 85 (1.28 g, >100%) as a red foam. The crude product was dissolved in dichloromethane. Silica gel was added to the dichloromethane solution and the suspension was concentrated in vacuo. The residue was loaded on top of a 90 g silica gel cartridge and eluted down the column using a solution of 20% ethyl acetate in hexane. Appropriate fractions of the major product were combined and concentrated in vacuo to give 85 (0.614 g, 58%) as a tan solid. This material was used in the next step without further purification.

1. stirringAfter stirring overnight
2. concentrationthe reaction was concentrated in vacuo
3. dissolutionThe residue was dissolved in ethyl acetate
4. washwashed once with water, three times with saturated aqueous
5. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-87b97b340bae4b149be2b83570b9d85c

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895752B2