ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-methoxyphenyl)pyroglutamate

Base Information

• Chemical Name: ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-methoxyphenyl)pyroglutamate
• CAS No.: 528607-22-9
• Molecular Formula: C₁₉H₂₅NO₆
• Molecular Weight: 363.411
• Mol file: 528607-22-9.mol

Synonyms:ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-methoxyphenyl)pyroglutamate

Chemical Property of ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-methoxyphenyl)pyroglutamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-methoxyphenyl)pyroglutamate

There total 2 articles about ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-methoxyphenyl)pyroglutamate 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:

di-tert-butyl dicarbonate (24424-99-5) + (2S,3R)-3-(4-Methoxy-phenyl)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester → ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-methoxyphenyl)pyroglutamate (528607-22-9)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃;

DOI:10.1021/jo0495438

Reference yield:

(2S,3R)-3-((p-methoxyphenyl))pyroglutamic acid (291763-96-7) → ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-methoxyphenyl)pyroglutamate (528607-22-9)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 20 °C

2: DMAP / acetonitrile / 20 °C

With dmap; thionyl chloride; In acetonitrile;

DOI:10.1021/jo0495438

Reference yield:

ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-methoxyphenyl)pyroglutamate (528607-22-9) → (2S,3R)-5-Hydroxy-3-(4-methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/jo0495438

upstream raw materials:

di-tert-butyl dicarbonate

(2S,3R)-3-((p-methoxyphenyl))pyroglutamic acid

Downstream raw materials:

(2S,3R)-3-(4-Methoxy-phenyl)-pyrrolidine-2-carboxylic acid ethyl ester

ethyl (2S,3R)-N-tert-butoxycarbonyl-3-(p-methoxyphenyl)prolinate