Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 17, 2004, Pages 4581-4583

  Kamal, Ahmed ^a   Sandbhor, Mahendra ^a   Ali Shaik, Ahmad ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

One pot lipase resolution; Propranolol; Sotalol

Indexed keywords

ACETIC ACID; ALCOHOL; ALPHA CHLOROHYDRIN; PROPRANOLOL; SOTALOL; TRIACYLGLYCEROL LIPASE;

ARTICLE; BURKHOLDERIA CEPACIA; CERAMICS; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

LIPASE; PROPRANOLOL; SOTALOL; STEREOISOMERISM;

BURKHOLDERIA CEPACIA; PSEUDOMONAS;

EID: 3843060381     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.05.084     Document Type: Article

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36. 23 The reaction was filtered through the pad of Celite, washed with water and brine and concentrated under reduced pressure. The crude compound was purified on column chromatography to get the corresponding alcohol 4 or 8 and acetate 5 or 9
37. 4ClS: C, 49.74; H, 5.57; N, 4.83; S, 11.06. Found: C, 49.22; H, 5.46; N, 4.67; S, 11.04%
38. 4d +35.8 ( c 1, water)]
39. (a) Enantioselectivity was determined by HPLC (CHIRACEL, AD-H column, Daicel). (a) Employing hexane/isopropanol = 90/10 as a mobile phase, with 0.5 mL/min flow rate and monitored at 254 nm wavelength
40. (b) Employing hexane/isopropanol/diethylamine = 90/10/0.1 as a mobile phase, with 0.5 mL/min flow rate and monitored at 254 nm wavelength
41. Enantioselectivity was determined by HPLC (CHIRACEL, OD column, Daicel) by employing hexane/isopropanol/diethylamine = 90/10/0.1 as a mobile phase, with 0.5 mL/min flow rate and monitored at 254 nm wavelength