(2S,3S)-3-(4-{2-[((R)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-ethyl}-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester

Base Information

• Chemical Name: (2S,3S)-3-(4-{2-[((R)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-ethyl}-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester
• CAS No.: 84426-19-7
• Molecular Formula: C₃₇H₃₈F₅N₃O₈
• Molecular Weight: 747.716
• Mol file: 84426-19-7.mol

Synonyms:

Chemical Property of (2S,3S)-3-(4-{2-[((R)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-ethyl}-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-(4-{2-[((R)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-ethyl}-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester

There total 10 articles about (2S,3S)-3-(4-{2-[((R)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-ethyl}-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester 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%

2,3,4,5,6-pentafluorophenol (771-61-9) + (2S,3S)-3-(4-{2-[((R)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-ethyl}-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (76847-36-4,76898-66-3) → (2S,3S)-3-(4-{2-[((R)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-ethyl}-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester (84426-19-7,84426-20-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; for 10h; Ambient temperature;

DOI:10.1002/jlac.198219821206

Reference yield:

di-tert-butyl oxalate (691-64-5) → (2S,3S)-3-(4-{2-[((R)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-ethyl}-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester (84426-19-7,84426-20-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / 1N NaOH / dioxane; H₂O / 3 h / Ambient temperature

2: Rh/ 5percent Al₂O₃, H₂ / ethanol; NH₃ / 12 h / Ambient temperature

3: 1N KHCO₃ / dioxane / 3 h / 0 °C

4: 80 percent / dicyclohexylcarbodiimide / ethyl acetate / 10 h / Ambient temperature

With sodium hydroxide; Rh/Al₂O₃; hydrogen; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; ethanol; ammonia; water; ethyl acetate;

DOI:10.1002/jlac.198219821206

Reference yield:

4-cyanomethylphenol (14191-95-8) → (2S,3S)-3-(4-{2-[((R)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-ethyl}-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester (84426-19-7,84426-20-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) Na, / 1) C₂H₅OH, 2) DMF, 16h, room temp.

2: 93 percent / 1N NaOH / dioxane; H₂O / 0.5 h

3: dimethylaminborane / acetic acid / 1 h / Ambient temperature

4: 90 percent / 1N NaOH / dioxane; H₂O / 3 h / Ambient temperature

5: Rh/ 5percent Al₂O₃, H₂ / ethanol; NH₃ / 12 h / Ambient temperature

6: 1N KHCO₃ / dioxane / 3 h / 0 °C

7: 80 percent / dicyclohexylcarbodiimide / ethyl acetate / 10 h / Ambient temperature

With sodium hydroxide; Rh/Al₂O₃; dimethylamine borane; hydrogen; sodium; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; ethanol; ammonia; water; acetic acid; ethyl acetate;

DOI:10.1002/jlac.198219821206

upstream raw materials:

2,3,4,5,6-pentafluorophenol

(2S,3S)-3-(4-{2-[((R)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-ethyl}-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

di-tert-butyl oxalate

4-cyanomethylphenol

Refernces

• 1、 Schmidt, Ulrich,Griesser, Helmut,Lieberknecht, Albrecht,Haeusler, Johannes. "Synthese des Dihydro-zizyphins G". . p. 272 - 273. Retrieved 2007/10/02.