(4-nitrophenyl)methyl N-[1-(3-sulfanylpyrrolidin-1-yl)ethylidene]carbamate

Base Information

• Chemical Name: (4-nitrophenyl)methyl N-[1-(3-sulfanylpyrrolidin-1-yl)ethylidene]carbamate
• CAS No.: 90505-36-5
• Molecular Formula: C14H17N3O4S
• Molecular Weight: 323.371
• European Community (EC) Number: 618-568-9
• Mol file: 90505-36-5.mol

Synonyms:ZQWBMXVEMVZOQI-UHFFFAOYSA-N;90505-36-5;A843567;3-Mercapto-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine;(4-nitrophenyl)methyl N-[1-(3-sulfanylpyrrolidin-1-yl)ethylidene]carbamate;N-[1-(3-mercapto-1-pyrrolidinyl)ethylidene]carbamic acid (4-nitrophenyl)methyl ester

Chemical Property of (4-nitrophenyl)methyl N-[1-(3-sulfanylpyrrolidin-1-yl)ethylidene]carbamate

Chemical Property:

• Boiling Point: 549.007 °C at 760 mmHg
• PKA: 10.10±0.20(Predicted)
• Flash Point: 285.83 °C
• PSA: 126.52000
• Density: 1.38 g/cm³
• LogP: 3.11500
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 323.09397721
• Heavy Atom Count: 22
• Complexity: 444

Purity/Quality:

99% ^*data from raw suppliers

N-[1-[(3S)-3-Mercapto-1-pyrrolidinyl]ethylidene]carbamicAcid(4-Nitrophenyl)methylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=NC(=O)OCC1=CC=C(C=C1)[N+](=O)[O-])N2CCC(C2)S
• Uses: (S)-[1-(3-Mercapto-1-pyrrolidinyl)ethylidene]carbamic acid (4-nitrophenyl)methyl ester is an intermediate used for the preparation of carbapenem antibiotic, a class of β-lactam antibiotics that exe rts a broad spectrum of antibacterial activity. N-[1-[(3S)-3-Mercapto-1-pyrrolidinyl]ethylidene]carbamic Acid (4-Nitrophenyl)methyl Ester is an intermediate used for the preparation of carbapenem antibiotic, a class of β-lactam antibiotics that exerts a broad spectrum of antibacterial activity.

Technology Process of (4-nitrophenyl)methyl N-[1-(3-sulfanylpyrrolidin-1-yl)ethylidene]carbamate

There total 4 articles about (4-nitrophenyl)methyl N-[1-(3-sulfanylpyrrolidin-1-yl)ethylidene]carbamate 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: 76.0%

3-(S)-acetylthio-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine (90505-35-4) → (S)-3-mercapto-1-pyrrolidine (90505-36-5)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 30h;

Reference yield:

3-(R)-hydroxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine (90512-67-7,915098-97-4) → (S)-3-mercapto-1-pyrrolidine (90505-36-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / triethylamine / CH₂Cl₂ / 0.5 h

2: 1.) NaH / 1.) DMF, 0 deg C, 10 min, 2.) DMF, 65 deg C, 3 h

3: 76 percent / sodium methoxide / methanol / 30 h / 0 °C

With sodium methylate; sodium hydride; triethylamine; In methanol; dichloromethane;

Reference yield:

3-(R)-methanesulfonyloxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine (90505-34-3) → (S)-3-mercapto-1-pyrrolidine (90505-36-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 10 min, 2.) DMF, 65 deg C, 3 h

2: 76 percent / sodium methoxide / methanol / 30 h / 0 °C

With sodium methylate; sodium hydride; In methanol;

upstream raw materials:

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

3-(R)-hydroxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine

3-(R)-methanesulfonyloxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine

4-nitrobenzyl chloroformate

Downstream raw materials:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thioacetic acid S-((S)-1-{1-[(Z)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-yl) ester

1-α-methyl RS-533

(4S,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5S,6S)-6-(1-Hydroxy-ethyl)-4-methoxy-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Refernces