cis-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-(benzyloxymethyl)azetidin-2-one

Base Information

• Chemical Name: cis-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-(benzyloxymethyl)azetidin-2-one
• CAS No.: 745074-71-9
• Molecular Formula: C₃₂H₃₇N₃O₄
• Molecular Weight: 527.663
• Mol file: 745074-71-9.mol

Synonyms:cis-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-(benzyloxymethyl)azetidin-2-one

Chemical Property of cis-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-(benzyloxymethyl)azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-(benzyloxymethyl)azetidin-2-one

There total 5 articles about cis-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-(benzyloxymethyl)azetidin-2-one 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: 95.0%

N-benzyl-N-benzyloxycarbonyl-glycine (71922-59-3) + (2R,5R)-1-[(2-benzyloxy)ethylideneamino]-2,5-dimethylpyrrolidine (745074-66-2) → cis-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-(benzyloxymethyl)azetidin-2-one (745074-71-9)

Guidance literature:

With 2-chloro-1-methyl-pyridinium iodide; N-ethyl-N,N-diisopropylamine; In toluene; at 40 ℃; for 29h;

DOI:10.1021/ol0490328

Reference yield:

(2S,5S)-2,5-hexanediol (34338-96-0) → cis-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-(benzyloxymethyl)azetidin-2-one (745074-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N / CH₂Cl₂ / 3 h / 0 °C

2.1: hydrazine monohydrate / 20 °C

2.2: 1.77 g / diethyl ether

3.1: i-Pr₂NEt; 2-chloro-N-methylpyridinium iodide / toluene / 38 h / 80 °C

With 2-chloro-1-methyl-pyridinium iodide; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;

DOI:10.1021/ol0490328

Reference yield:

(S,S)-2,5-bis(methylsulfonyloxy)hexane (119008-52-5) → cis-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-(benzyloxymethyl)azetidin-2-one (745074-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrazine monohydrate / 20 °C

1.2: 1.77 g / diethyl ether

2.1: i-Pr₂NEt; 2-chloro-N-methylpyridinium iodide / toluene / 38 h / 80 °C

With 2-chloro-1-methyl-pyridinium iodide; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; In toluene;

DOI:10.1021/ol0490328

upstream raw materials:

N-benzyl-N-benzyloxycarbonyl-glycine

(2R,5R)-1-[(2-benzyloxy)ethylideneamino]-2,5-dimethylpyrrolidine

(S,S)-2,5-bis(methylsulfonyloxy)hexane

(2S,5S)-2,5-hexanediol

Downstream raw materials:

cis-(3R,4R)-3-[benzyl(benzyloxycarbonyl)amino]-4-(benzyloxymethyl)azetidin-2-one