[N(E)]-[1-[(3S)-3-Hydroxy-1-pyrrolidinyl]ethylidene]carbamic acid (4-nitrophenyl)methyl ester

Base Information

• Chemical Name: [N(E)]-[1-[(3S)-3-Hydroxy-1-pyrrolidinyl]ethylidene]carbamic acid (4-nitrophenyl)methyl ester
• CAS No.: 915098-97-4
• Molecular Formula: C₁₄H₁₇N₃O₅
• Molecular Weight: 307.306
• Mol file: 915098-97-4.mol

Synonyms:[N(E)]-[1-[(3S)-3-Hydroxy-1-pyrrolidinyl]ethylidene]carbamic acid (4-nitrophenyl)methyl ester

Chemical Property of [N(E)]-[1-[(3S)-3-Hydroxy-1-pyrrolidinyl]ethylidene]carbamic acid (4-nitrophenyl)methyl ester

Chemical Property:

• PSA: 107.95000
• Density: 1.38
• LogP: 2.17750

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [N(E)]-[1-[(3S)-3-Hydroxy-1-pyrrolidinyl]ethylidene]carbamic acid (4-nitrophenyl)methyl ester

There total 5 articles about [N(E)]-[1-[(3S)-3-Hydroxy-1-pyrrolidinyl]ethylidene]carbamic acid (4-nitrophenyl)methyl 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: 75.0%

3-(S)-benzoyloxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine (105622-52-4) → 3-(S)-hydroxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine (90505-37-6,915098-97-4)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 0 ℃; for 2h;

Reference yield:

ethyl acetimidate hydrochloride (2208-07-3) + 3-hydroxypyrrolidine hydrochloride (111810-68-5) + 4-nitrobenzyl chloroformate (4457-32-3) → 3-hydroxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine (86063-92-5,915098-97-4)

Guidance literature:

With triethylamine; In ethanol; dichloromethane; water; ethyl acetate; benzene;

Reference yield:

3-(R)-hydroxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine (90512-67-7,915098-97-4) → 3-(S)-hydroxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine (90505-37-6,915098-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 2 h / Ambient temperature

2: 75 percent / NaOCH₃ / tetrahydrofuran; methanol / 2 h / 0 °C

With sodium methylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol;

upstream raw materials:

ethyl acetimidate hydrochloride

(R)-3-hydroxypyrrolidine hydrochloride

4-nitrobenzyl chloroformate

3-(S)-benzoyloxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine

Refernces

• 1、 -. "Carbapenem compounds, and compositions containing them". . . Retrieved 2008/06/13.