185692-85-7

Pale Yellow Oil

Intermediate in the synthesis of Chloramphenicol (C325030).

The general procedure for the synthesis of tert-butyl (S)-((1-((tert-butyldimethylmethylsilyl)oxy)-3-hydroxypropan-2-yl)carbamate, using the compound (CAS:112418-19-6) as a starting material, was as follows: to a solution of tetrahydrofuran (THF, 150 ml) of the product obtained in step 3 (16.5 g, 45.6 mmol) was slowly added a 2 M THF solution of lithium borohydride (37.1 ml). The reaction mixture was stirred at room temperature for 2.5 hours. After completion of the reaction, the reaction was quenched with saturated ammonium chloride (NH4Cl) solution and extracted with ethyl acetate (EtOAc, 2 x 250 ml). The combined organic layers were washed sequentially with saturated ammonium chloride solution (100 ml), saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the target product (14.5 g, 100% yield). Mass spectrometry (MS) analysis showed m/e 306 (M + H)+.

[1] Patent: WO2006/14762, 2006, A1. Location in patent: Page/Page column 42
[2] Patent: WO2006/14944, 2006, A1. Location in patent: Page/Page column 32
[3] European Journal of Organic Chemistry, 2013, # 31, p. 7145 - 7151
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4204 - 4219
[5] Patent: WO2008/86122, 2008, A2. Location in patent: Page/Page column 68