Реакция #645236

Уравнение реакции

1-methylthiocarbonyloxyethyl benzoate

Methylthiocarbonyloxyethyl benzoate

phosphate buffered saline

(R)-(−)-2,2,2-trifluoro-1-(9-anthryl)ethanol

→

title compound ( 5 )

(1R)-1-Methylthiocarbonyloxyethyl benzoate

Растворители

ether

Условия реакции

Обработка

1. 1
   Другоеthe ether layer separated
2. 2
   Фильтрацияfiltered through a pad of CELITE® 545
3. 3
   Другоеto remove the enzyme
4. 4
   ПромывкаThe ether layer was washed with aqueous sodium bicarbonate (NaHCO3) (5 times) and brine
5. 5
   Сушкаdried over anhydrous sodium sulfate (Na2SO4)
6. 6
   ДругоеAfter the solvent was removed by rotary evaporation

Методика

A mixture of 1-methylthiocarbonyloxyethyl benzoate (2g) (50 g) and lipase from Candida rugosa (2.50 g) in pH 7.2 phosphate buffered saline (500 mL) was stirred at room temperature. The reaction was monitored by 1H-NMR using the chiral solvating agent (R)-(−)-2,2,2-trifluoro-1-(9-anthryl)ethanol. The reaction was complete after ca. 12 hours. The reaction mixture was diluted with ether and the ether layer separated and filtered through a pad of CELITE® 545 to remove the enzyme. The ether layer was washed with aqueous sodium bicarbonate (NaHCO3) (5 times) and brine, and dried over anhydrous sodium sulfate (Na2SO4). After the solvent was removed by rotary evaporation, 22 g of the title compound (5) was obtained. 1H-NMR using a chiral solvating agent showed a single isomer and the absolute configuration was confirmed by derivatization to a compound having a known stereochemistry. 1H-NMR (CDCl3): δ 1.65 (d, J=5.6 Hz, 3H), 2.35 (s, 3H), 7.20 (q, J=5.6 Hz, 1H), 7.45 (m, 2H), 7.58 (m, 1H), 8.06 (m, 2H) ppm.

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