(S)-(-)-2-HYDROXY-1,2,2-TRIPHENYLETHYL ACETATE synthesis

Yield: 93%

Reaction Conditions:

with pyridine in dichloromethane for 2.08 h;Inert atmosphere;Cooling with ice;

Steps:

2 Example 2 Hytra
S)-1,1,2-Triphenylethane-1,2-diol (Alfa Aesar, 9.5 g, 32.7 mmol) was dissolved in dichloromethane (200 mL) under an argon atmosphere. The flask was cooled in an ice-water bath, and acetyl chloride (6.0 g, 76.4 mmol) was added. Pyridine (8.0 g, 82 mmol) was added drop-wise over 5 minutes. After 2 hours, the product was filtered. The product was dissolved in dichloromethane (2 L) and extracted with 5% aqueous hydrochloric acid (150 mL) and water (150 mL). The dichloromethane solution was dried over anhydrous sodium sulfate, filtered, concentrated (to 40 mL) and stored in a freezer for two hours. The solid product was collected on a funnel, washed with dichloromethane (15 mL) and dried under high vacuum overnight. The experiment produced Hytra as a white solid (10.1 g, 93% yield) and is characterized by the following spectra: (0053) ¹H NMR (300 MHz, DMSO-d₆): δ 7.48 (d, 2H, J=7.5 Hz), 7.33-7.23 (m, 5H), 7.18-7.05 (m, 8H), 6.58 (s, 1H), 6.14 (s, 1H), 1.93 (s, 3H).

References:

Jiva Pharma, Inc.;Goel, Om P US2015/322032, 2015, A1 Location in patent:Paragraph 0051-0053