115538-83-5

Usage

Uses

Used in Pharmaceutical Industry:
2-[4-(3-CHLORO-2-HYDROXYPROPOXY)PHENYL]ACETAMIDE is used as an impurity in the manufacturing process of Atenolol (A790075), a cardioselective β-adrenergic blocker. Its presence is significant as it can affect the purity and efficacy of the final pharmaceutical product. The compound is essential for quality control and assurance in the production of Atenolol, ensuring the safety and effectiveness of the medication for patients with cardiovascular conditions.

Upstream product

• 17194-82-0 2-(4-hydroxyphenyl)acetamide 
• 106-89-8 epichlorohydrin 
• 143925-21-7 1--2-acetoxy-3-chloropropane 
• 29122-69-8 (S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane 
• 75-36-5 acetyl chloride 

Downstream Products

• 56715-13-0 (+)-(R)-atenolol 
• 93379-54-5 (S)-Atenolol 
• 143925-21-7 1--2-acetoxy-3-chloropropane 
• 29122-68-7 (RS)-atenolol 

Relevant academic research and scientific papers

Highly enantioselective CALB-catalyzed kinetic resolution of building blocks for β-blocker atenolol

Both enantiomers of 4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide has been synthesized in 98.5–99% enantiomeric excess by use of lipase B from Candida antarctica as catalyst. The R-alcohol is a building block for the cardioselective β-blocker (S)-atenolol ((S)-2-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide. Performing kinetic resolutions of 3-chloro-1-phenoxy-2-propanol and 3-bromo-1-phenoxy-2-propanol with vinyl butanoate as acyl donor and the same CALB enzyme, but a different preparation, showed higher E-values than previously reported.

Lipase-catalyzed green synthesis of enantiopure atenolol

A new green route is proposed for the synthesis of enantiopure atenolol (a β1-blocker). An enzymatic kinetic resolution approach was used to synthesize the enantiopure intermediates (R)- and (S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide from the corresponding racemic alcohol. Of the commercially available lipases screened, Candida antarctica lipase-A (CLEA) showed maximum enantioselectivity in the transesterification of the racemic alcohol using vinyl acetate as the acyl donor. The reactions afforded the (S)-alcohol along with the (R)-acetate, with 48.9% conversion (E = 210, eeP = 96.9% and eeS = 91.1%). Various reaction parameters were optimized in order to achieve maximum enantioselectivity. N-alkylation of the (S)-alcohol with isopropylamine afforded the (S)-atenolol, and the (R)-acetate was chemically hydrolyzed to the corresponding alcohol and further converted to the (R)-atenolol via N-alkylation of the (R)-alcohol with isopropylamine. The use of ionic liquids, to solve the solubility related problems of the drug intermediates, made this process greener and more efficient compared to the previously reported methods. This journal is