56715-12-9

Basic information

• Product Name: 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide
• Synonyms: 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide;2-[4-[[(2S)-oxiran-2-yl]methoxy]phenyl]acetamide
• CAS NO: 56715-12-9
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.22582
• Product Categories: Amines, Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 56715-12-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Solubility: Methanol
• CAS DataBase Reference: 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide(56715-12-9)
• EPA Substance Registry System: 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide(56715-12-9)

Safety Data

• Hazardous Substances Data: 56715-12-9(Hazardous Substances Data)

Usage

Description

4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals. It is characterized by its unique chemical structure, which includes a benzene ring, an acetamide group, and a 2-oxiranylmethoxy group attached to the 4-position of the benzene ring. 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide plays a significant role in the development of specific medications, particularly in the field of cardiovascular health.

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

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

Downstream Products

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

Relevant articles and documents

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 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.

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.