Ethyl 2-((2R,3S)-N-(4-methoxyphenyl)-3-methyloxirane-2-carboxamido)acetate

Base Information

• Chemical Name: Ethyl 2-((2R,3S)-N-(4-methoxyphenyl)-3-methyloxirane-2-carboxamido)acetate
• CAS No.: 203790-61-8
• Molecular Formula: C15H19NO5
• Molecular Weight: 293.32
• Mol file: 203790-61-8.mol

Synonyms:(2R,3R)-N-(4-chloro-phenyl)-2,3-dihydroxysuccinamic acid;;L-TACA;;ethyl 2-((2R,3R)-N-(4-methoxyphenyl)-3-methyloxirane-2-carboxamido)acetate;;(R,R)-(+)-4-chlorotartranilic acid;;

Chemical Property of Ethyl 2-((2R,3S)-N-(4-methoxyphenyl)-3-methyloxirane-2-carboxamido)acetate

Chemical Property:

• PSA: 79.37000
• LogP: 2.66380

Purity/Quality:

97% ^*data from raw suppliers

Ethyl2-((2R,3S)-N-(4-methoxyphenyl)-3-methyloxirane-2-carboxamido)acetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethyl 2-((2R,3S)-N-(4-methoxyphenyl)-3-methyloxirane-2-carboxamido)acetate

There total 2 articles about Ethyl 2-((2R,3S)-N-(4-methoxyphenyl)-3-methyloxirane-2-carboxamido)acetate 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: 80.0%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + N-(4-methoxy)phenylglycine ethyl ester (50845-77-7) → N-(4-methoxyphenyl)-2-[(2R,3R)-2,3-epoxybutyramidyl]acetic acid ethyl ester (203790-61-8)

Guidance literature:

L-threonine; With hydrogenchloride; sodium nitrite;

N-(4-methoxy)phenylglycine ethyl ester; With chloroformic acid ethyl ester; triethylamine;

DOI:10.1007/s11164-011-0344-5

Reference yield:

N-(4-methoxy)phenylglycine ethyl ester (50845-77-7) + (2R,3R)-2,3-epoxybutanoic acid (86561-72-0) → N-(4-methoxyphenyl)-2-[(2R,3R)-2,3-epoxybutyramidyl]acetic acid ethyl ester (203790-61-8)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 25 ℃; for 2.5h;

Reference yield:

N-(4-methoxyphenyl)-2-[(2R,3R)-2,3-epoxybutyramidyl]acetic acid ethyl ester (203790-61-8) → ethyl (3S)-3-((R)-1-hydroxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate

Guidance literature:

N-(4-methoxyphenyl)-2-[(2R,3R)-2,3-epoxybutyramidyl]acetic acid ethyl ester; With zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; at -15 - 0 ℃;

With hydrogenchloride; water; In tetrahydrofuran; dichloromethane; Product distribution / selectivity;

upstream raw materials:

N-(4-methoxy)phenylglycine ethyl ester

(2R,3R)-2,3-epoxybutanoic acid

L-threonine

Downstream raw materials:

ethyl (3S)-3-((R)-1-hydroxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate