(5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline

Base Information

• Chemical Name: (5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline
• CAS No.: 1033714-59-8
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293
• Mol file: 1033714-59-8.mol

Synonyms:(5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline

Chemical Property of (5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline

There total 5 articles about (5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline 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: 100.0%

1-benzyl 2-tert-butyl (2S,5R)-5-methylpyrrolidine-1,2-dicarboxylate (1033714-55-4) → (5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline (1033714-59-8)

Guidance literature:

With trifluoroacetic acid; In chloroform; at 50 ℃; for 16h;

DOI:10.1016/j.bmc.2013.04.056

Reference yield:

Cbz-L-pGlu-OH (32159-21-0) → (5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline (1033714-59-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: perchloric acid / water / 16 h / 20 °C

2.1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / 48 h / 20 °C

4.1: copper(I) bromide dimethylsulfide complex / diethyl ether / 0.5 h / -78 °C / Inert atmosphere

4.2: 16 h / -78 - 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / chloroform / 16 h / 50 °C

With perchloric acid; copper(I) bromide dimethylsulfide complex; lithium triethylborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; chloroform; water;

DOI:10.1016/j.bmc.2013.04.056

Reference yield:

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1) → (5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline (1033714-59-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / 48 h / 20 °C

3.1: copper(I) bromide dimethylsulfide complex / diethyl ether / 0.5 h / -78 °C / Inert atmosphere

3.2: 16 h / -78 - 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / chloroform / 16 h / 50 °C

With copper(I) bromide dimethylsulfide complex; lithium triethylborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; chloroform;

DOI:10.1016/j.bmc.2013.04.056

upstream raw materials:

1-benzyl 2-tert-butyl (2S,5R)-5-methylpyrrolidine-1,2-dicarboxylate

Cbz-L-pGlu-OH

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate

1-benzyl 2-tert-butyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(5R,6S)-5,6-bis(4-chlorophenyl)-2-[((2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidin-1-yl)carbonyl]-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole

benzyl (2S,5R)-2-{[(3S)-3,4-dimethylpiperazin-1-yl]carbonyl}-5-methylpyrrolidine-1-carboxylate

Refernces