4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide

Base Information

• Chemical Name: 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide
• CAS No.: 56715-12-9
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.229
• Mol file: 56715-12-9.mol

Synonyms:(S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide

Chemical Property of 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide

Chemical Property:

• Solubility.: Methanol

Purity/Quality:

4-[(2S)-2-Oxiranylmethoxy]benzeneacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-[(2S)-2-Oxiranylmethoxy]benzeneacetamide is an intermediate in the synthesis of (S)-Atenolol (A790085), a cardioselective β-adrenergic blocker.

Technology Process of 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide

There total 9 articles about 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

4-acetaminophenol (103-90-2,8055-08-1) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) → (S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide (56715-12-9)

Guidance literature:

With cesium fluoride; In water;

Reference yield: 95.0%

2-(4-hydroxyphenyl)acetamide (17194-82-0) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) → (S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide (56715-12-9)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; at 25 ℃; for 12h;

DOI:10.1016/S0040-4020(99)00896-0

Reference yield: 95.0%

2-(4-hydroxyphenyl)acetamide (17194-82-0) + S-oxiran-2-ylmethyl 4-nitrobenzenesulfonate (118712-60-0,118629-64-4) → (S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide (56715-12-9)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; for 14h; Ambient temperature;

DOI:10.1016/S0040-4039(98)00452-3

upstream raw materials:

(R)-(-)-epichlorohydrin

2-(4-hydroxyphenyl)acetamide

(S)-Glycidyl tosylate

S-oxiran-2-ylmethyl 4-nitrobenzenesulfonate

Downstream raw materials:

(+)-(R)-atenolol

(S)-Atenolol

Refernces

• 1、 -. "Process for producing atenolol of high optical purity". Page/Page column 5-6; 8-9; 11. . Retrieved 2008/06/13.
• 2、 -. "Process for the preparation of 3-amino-2-hydroxy-1-propyl ethers". . . Retrieved 2008/06/13.