反応 #645236

反応方程式

1-methylthiocarbonyloxyethyl benzoate

Methylthiocarbonyloxyethyl benzoate

phosphate buffered saline

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

→

title compound ( 5 )

(1R)-1-Methylthiocarbonyloxyethyl benzoate

溶媒

ether

反応条件

後処理

1. 1
   その他the ether layer separated
2. 2
   ろ過filtered through a pad of CELITE® 545
3. 3
   その他to remove the enzyme
4. 4
   洗浄The ether layer was washed with aqueous sodium bicarbonate (NaHCO3) (5 times) and brine
5. 5
   乾燥dried over anhydrous sodium sulfate (Na2SO4)
6. 6
   その他After the solvent was removed by rotary evaporation

実験手順

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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