Vinyl Acetate → (S)-3-hydroxy-3-(2-thienyl) propanenitrile

Enzymatic Transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile (1): To a solution of 3-hydroxy-3-(2-thienyl) propanenitrile (1) (5 mmol) dissolved in diisopropyl ether (100 mL), Pseudomonas cepacia lipase immobilized on diatomite (PS-D) (500 mg) and vinyl acetate (25 mmol) were added successively and incubated at 25° C. in an orbital shaker. After 50% completion of the reaction (14 h) as indicated by HPLC, the reaction mixture was filtered and solvent was evaporated under reduced pressure. The residue was subjected to column chromatography to separate the acetate formed and the unreacted alcohol. The optical purity of these compounds were determined by HPLC. (S)-3-hydroxy-3-(2-thienyl) propanenitrile (S-1) 42% yield, ee>99%; [α]30D=−33.5 (c 1, CHCl3); IR (Neat) 3475, 3075, 2878, 2251, 1105, 698 cm−1; 1H NMR (200 MHz, CDCl3) δ 2.82 (dd, 2H, J=3.0 Hz, J=6.6 Hz), 3.0 (s, 1H) 5.25 (t, 1H, J=5.5 Hz), 6.98 (t, 1H, J=4.9 Hz), 7.05 (d, 1H, J=3.7 Hz), 7.28 (d, 1H, J=4.9 Hz); 13C NMR (75 MHz) δ 28.1, 66.0, 117.0, 124.6, 125.6, 127.0, 144.4; Mass (EI) 153 127, 113, 85.

1. additionwere added successively
2. customincubated at 25° C. in an orbital shaker
3. customAfter 50% completion of the reaction (14 h)
4. filtrationthe reaction mixture was filtered
5. customsolvent was evaporated under reduced pressure
6. customto separate the acetate
7. customformed

ORD 기록

ord-f676916710c94bbb8cfbcd6cbbaddd11

출처 데이터셋

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07045341B2