反応 #645235

反応方程式

2-methyl-1-methylthiocarbonyloxypropyl 2-methylpropanoate

2-Methyl-1-methylthiocarbonyloxypropyl 2-methylpropanoate

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

→

title compound ( 4 )

収率 24.3%

(1R)-2-Methyl-1-methylthiocarbonyloxypropyl 2-methylpropanoate

収率 24.3%

溶媒

ether

phosphate buffered saline

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction was stirred overnight
2. 2
   その他the ether layer separated
3. 3
   ろ過filtered through a pad of CELITE® 545
4. 4
   その他to remove the enzyme
5. 5
   洗浄The ether layer was washed with aqueous sodium bicarbonate (NaHCO3) (5 times) and brine
6. 6
   乾燥dried over anhydrous sodium sulfate (Na2SO4)
7. 7
   その他After rotary evaporation
8. 8
   その他to remove the solvent

実験手順

A mixture of 2-methyl-1-methylthiocarbonyloxypropyl 2-methylpropanoate (2b) (125 g) and lipase from Candida rugosa (Sigma-Aldrich) (12.5 g) in pH 7.2 phosphate buffered saline (1 L) 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 stirred overnight. The reaction mixture was then 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 rotary evaporation to remove the solvent, 30.4 g of the title compound (4) was obtained. 1H-NMR using a chiral solvating agent confirmed the presence of a single isomer. The absolute configuration was determined by derivatization to a compound having known stereochemistry. 1H-NMR (CDCl3): δ 0.96 (d, J=6.8 Hz, 6H), 1.16 (d, J=6.8 Hz, 3H), 1.17 (d, J=6.8 Hz, 3H), 1.98-2.07 (m, 1H), 2.32 (s, 3H), 2.56 (septet, J=7.2 Hz, 1H), 6.67 (d, J=5.6 Hz, 1H) ppm.

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