(2'S,4'R)-methyl 1'-((S)-2-tert-butoxycarbonyl)amino-4-methylpentanoyl-4'-hydroxypyrrolidine-2'-carboxylate

Base Information

• Chemical Name: (2'S,4'R)-methyl 1'-((S)-2-tert-butoxycarbonyl)amino-4-methylpentanoyl-4'-hydroxypyrrolidine-2'-carboxylate
• CAS No.: 934552-55-3
• Molecular Formula: C₁₇H₃₀N₂O₆
• Molecular Weight: 358.435
• Mol file: 934552-55-3.mol

Synonyms:(2'S,4'R)-methyl 1'-((S)-2-tert-butoxycarbonyl)amino-4-methylpentanoyl-4'-hydroxypyrrolidine-2'-carboxylate

Chemical Property of (2'S,4'R)-methyl 1'-((S)-2-tert-butoxycarbonyl)amino-4-methylpentanoyl-4'-hydroxypyrrolidine-2'-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S,4'R)-methyl 1'-((S)-2-tert-butoxycarbonyl)amino-4-methylpentanoyl-4'-hydroxypyrrolidine-2'-carboxylate

There total 2 articles about (2'S,4'R)-methyl 1'-((S)-2-tert-butoxycarbonyl)amino-4-methylpentanoyl-4'-hydroxypyrrolidine-2'-carboxylate 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: 81.0%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2'S,4'R)-methyl 1'-((S)-2-tert-butoxycarbonyl)amino-4-methylpentanoyl-4'-hydroxypyrrolidine-2'-carboxylate (934552-55-3)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 13h;

DOI:10.1016/j.bmcl.2015.10.075

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) + Boc-L-Leu-OBt (93957-20-1) → (2'S,4'R)-methyl 1'-((S)-2-tert-butoxycarbonyl)amino-4-methylpentanoyl-4'-hydroxypyrrolidine-2'-carboxylate (934552-55-3)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmc.2007.01.020

Reference yield:

(2'S,4'R)-methyl 1'-((S)-2-tert-butoxycarbonyl)amino-4-methylpentanoyl-4'-hydroxypyrrolidine-2'-carboxylate (934552-55-3) → (3S,7R,8aS)-3-isobutyloctahydropyrrolo[1,2-a]pyrazine-7-ol (1222778-67-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 3 h

1.2: 16 h / Reflux

2.1: iodine; sodium tetrahydroborate / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

With sodium tetrahydroborate; iodine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2016.12.002

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

Boc-L-Leu-OBt

N-tert-butoxycarbonyl-L-leucine

Downstream raw materials:

(3S,7R,8aS)-3-isobutyloctahydropyrrolo[1,2-a]pyrazine-7-ol