反応 #645244

反応方程式

1-Methylthiocarbonyloxyethyl benzoate

Methylthiocarbonyloxyethyl benzoate

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

phosphate buffered saline

→

title compound ( 5 )

(1R)-1-Methylthiocarbonyloxyethyl benzoate

溶媒

ether

反応条件

後処理

1. 1
   その他at room temperature
2. 2
   その他the ether layer separated
3. 3
   ろ過filtered through a pad of CELITE®
4. 4
   その他to remove the enzyme
5. 5
   洗浄The ether phase was washed repeatedly with aqueous sodium bicarbonate
6. 6
   乾燥brine, and dried over anhydrous sodium sulfate (Na2SO4)
7. 7
   その他Removing the solvent in vacuo

実験手順

1-Methylthiocarbonyloxyethyl benzoate (2g) (50 g), prepared as described in Gallop et al., U.S. Pat. No. 7,227,028, and lipase from Candida rugosa (2.5 g) were stirred in phosphate buffered saline, pH 7.2, (0.5 L) at room temperature. The progress of the reaction was monitored by 1H-NMR using the chiral solvating agent [(R)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol] and was complete within 16 h. The reaction mixture was diluted with ether and the ether layer separated and filtered through a pad of CELITE® to remove the enzyme. The ether phase was washed repeatedly with aqueous sodium bicarbonate then brine, and dried over anhydrous sodium sulfate (Na2SO4). Removing the solvent in vacuo afforded 22 g of the title compound (5) as a single enantiomer. 1H NMR (CDCl3, 400 MHz): 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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