pyrrolidine-2-carboxylic acid 1-{[1-(1-{[1-(1-{[1-(1-benzyloxycarbonyl-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethyl ester

Base Information

• Chemical Name: pyrrolidine-2-carboxylic acid 1-{[1-(1-{[1-(1-{[1-(1-benzyloxycarbonyl-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethyl ester
• CAS No.: 188908-27-2
• Molecular Formula: C₅₇H₇₈N₄O₁₃
• Molecular Weight: 1027.27

Synonyms:pyrrolidine-2-carboxylic acid 1-{[1-(1-{[1-(1-{[1-(1-benzyloxycarbonyl-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethyl ester

Chemical Property of pyrrolidine-2-carboxylic acid 1-{[1-(1-{[1-(1-{[1-(1-benzyloxycarbonyl-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of pyrrolidine-2-carboxylic acid 1-{[1-(1-{[1-(1-{[1-(1-benzyloxycarbonyl-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethyl ester

There total 12 articles about pyrrolidine-2-carboxylic acid 1-{[1-(1-{[1-(1-{[1-(1-benzyloxycarbonyl-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethyl 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: 90.0%

C62H86N4O15 (188908-26-1) → pyrrolidine-2-carboxylic acid 1-{[1-(1-{[1-(1-{[1-(1-benzyloxycarbonyl-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethyl ester (188908-27-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 1h;

DOI:10.1021/jm020482k

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → pyrrolidine-2-carboxylic acid 1-{[1-(1-{[1-(1-{[1-(1-benzyloxycarbonyl-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethyl ester (188908-27-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / DIC; DMAP / CH₂Cl₂ / 1 h / 20 °C

2: 70 percent / aq. NaOH / methanol / 0.33 h / 20 °C

3: 82 percent / DIC; DMAP / CH₂Cl₂ / 16 h / 20 °C

4: 98 percent / H₂ / Pd/C / ethanol / 3 h / 2327.17 - 2585.74 Torr

5: 61 percent / DCC; DMAP / CH₂Cl₂ / 3 h / 20 °C

6: 90 percent / CF₃CO₂H / CH₂Cl₂ / 1 h / 25 °C

With dmap; sodium hydroxide; hydrogen; dacarbazine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane;

DOI:10.1021/jm020482k

Reference yield:

benzyl N-methyl-L-leucyl-3-phenyl-D-lactate (157567-63-0) → pyrrolidine-2-carboxylic acid 1-{[1-(1-{[1-(1-{[1-(1-benzyloxycarbonyl-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-2-phenyl-ethoxycarbonyl)-3-methyl-butyl]-methyl-carbamoyl}-ethyl ester (188908-27-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / DIC; DMAP / CH₂Cl₂ / 16 h / 20 °C

2: 98 percent / H₂ / Pd/C / ethanol / 3 h / 2327.17 - 2585.74 Torr

3: 61 percent / DCC; DMAP / CH₂Cl₂ / 3 h / 20 °C

4: 90 percent / CF₃CO₂H / CH₂Cl₂ / 1 h / 25 °C

With dmap; hydrogen; dacarbazine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/jm020482k

upstream raw materials:

C₆₂H₈₆N₄O₁₅

1-(tert-butoxycarbonyl)-L-proline

(R)-2-((S)-2-(tert-butoxycarbonyl(methyl)amino)-4-methylpentanoyloxy)propanoic acid

benzyl N-methyl-L-leucyl-3-phenyl-D-lactate

Downstream raw materials:

L-prolyl-D-lactyl-N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactyl-N-methyl-L-leucyl-3-phenyl-D-lactic acid

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