56715-12-9

Usage

Uses

Used in Pharmaceutical Industry:
4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide is used as an intermediate in the synthesis of (S)-Atenolol (A790085), a cardioselective β-adrenergic blocker. This application is significant because (S)-Atenolol is an essential medication for the treatment of various cardiovascular conditions, such as hypertension and angina pectoris. 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide's role in the synthesis process is crucial, as it contributes to the development of a drug that can effectively manage and prevent cardiac-related issues.

Upstream product

• 51594-55-9 (R)-(-)-epichlorohydrin 
• 17194-82-0 2-(4-hydroxyphenyl)acetamide 
• 70987-78-9 (S)-Glycidyl tosylate 
• 118712-60-0 S-oxiran-2-ylmethyl 4-nitrobenzenesulfonate 
• 67843-74-7 (S)-epichlorohydrin 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 103-90-2 4-acetaminophenol 
• 106-89-8 epichlorohydrin 

Downstream Products

• 56715-13-0 (+)-(R)-atenolol 
• 93379-54-5 (S)-Atenolol 

Relevant academic research and scientific papers

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

Process for producing atenolol of high optical purity

The present invention relates to an improved process for producing optically active (S)-atenolol of formula (1) in high optical purity by reacting a phenol with an epichlorohydrin.

Process for the preparation of 3-amino-2-hydroxy-1-propyl ethers

PCT No. PCT/JP97/03220 Sec. 371 Date Apr. 28, 1999 Sec. 102(e) Date Apr. 28, 1999 PCT Filed Sep. 12, 1997 PCT Pub. No. WO98/12171 PCT Pub. Date Mar. 26, 1998A process for preparation of 3-amino-2-hydroxy-1-propyl ether of the formula wherein R1 is substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic ring, R2 and R3 are the same or different hydrogen atom, a substituted or unsubstituted alkyl, or may form a ring together with an adjacent nitrogen atom, which ring may be interrupted with nitrogen atom, oxygen atom or sulfur atom, which is characterized in reacting an epoxy compound of the formula wherein X is halogen, in the presence of a fluoride salt, with an alcohol and then reacting an amine. According to the above method, an intermediates for synthesis of medicines is obtained in good yield and highly optical purity.

Process for preparation of glycidyl ether

PCT No. PCT/JP97/03221 Sec. 371 Date Apr. 29, 1999 Sec. 102(e) Date Apr. 29, 1999 PCT Filed Sep. 12, 1997 PCT Pub. No. WO98/12186 PCT Pub. Date Mar. 26, 1998A process for preparation of a glycidyl ether which is characrelized in reacting an epoxy compound of the formula wherein X is halogen or sulfonyloxy in the presence of a fluoride salt, with an alcohol. According to the above method, glycigyl ethers or their optically active compounds important as intermediates for synthesis of medicines are easily obtained in good yield and especially the optically active compounds are obtained with highly optical purity.

CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers

The two modes of the paths in the reaction of oxiranes with phenols are completely controlled by CsF. Glycidyl nosylate undergoes exclusive substitution at the C1 position whereas the ring-opening (C-3 attack) occurs with epichlorohydrin, glycidol, and 1,2-epoxyalkanes. These reactions provide convenient access to enantiopure β-blockers.

One pot synthesis of (±)/(S)-atenolol and (±)/(S)-propranolol by employing polymer supported reagent

(±)/(S)-Atenolol and (±)/(S)-propranolol were synthesized by using reaction of (±)/(S)-epichlorohydrin with polymer supported phenoxide anion followed by reaction with isopropylamine.

CsF in organic synthesis. The first and convenient synthesis of enantiopure bisoprolol by use of glycidyl nosylate

The regioselective substitution of glycidyl nosylate with phenols is catalyzed by CsF in the presence of K2CO3 in DMF; this reaction enables the first and convenient synthesis of enantiopure bisoprolol.

A practical synthesis of optically active atenolol from chiral epichlorohydrin

The synthesis of (R)- and (S)-atenolol (1) was achieved in two steps starting from p-hydroxyphenylacetamide (2). Both enantiomers of the glycidyl ether 4 were synthesized from 2 and (R)- and (S)-epichlorohydrin (3) using an alkali metal hydroxide and/or BTA (benzyltrimethylammonium chloride), respectively. Subsequent treatment of 4 with isopropylamine afforded atenolol (1) with excellent enantiomeric excess (> 98% ee).