(4-nitrophenyl)methyl (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: (4-nitrophenyl)methyl (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 29124-83-2
• Molecular Formula: C15H15 N3 O5 S
• Molecular Weight: 349.367
• European Community (EC) Number: 249-454-3
• Nikkaji Number: J250.771D
• Mol file: 29124-83-2.mol

Synonyms:29124-83-2;SCHEMBL9656363;(6R,6beta)-7alpha-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

Chemical Property of (4-nitrophenyl)methyl (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

• Vapor Pressure: 5.9E-15mmHg at 25°C
• Boiling Point: 612.8°Cat760mmHg
• Flash Point: 324.4°C
• PSA: 143.75000
• Density: 1.51g/cm³
• LogP: 2.31580
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 349.07324176
• Heavy Atom Count: 24
• Complexity: 594

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N2C(C(C2=O)N)SC1)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-]
• Isomeric SMILES: CC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-]

Technology Process of (4-nitrophenyl)methyl (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 7 articles about (4-nitrophenyl)methyl (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-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:

(6R)-3-methyl-8-oxo-7t-(3-oxo-3H-isobenzofuran-1-ylideneamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester (55151-66-1) → p-nitrobenzyl ester of 7-aminodeacetoxycephalosporanic acid (29124-83-2)

Guidance literature:

With hydrazine; In tetrahydrofuran;

DOI:10.1021/ja00852a044

Reference yield:

(6R)-3-methyl-8-oxo-7t-phthalimido-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester (51415-20-4) → p-nitrobenzyl ester of 7-aminodeacetoxycephalosporanic acid (29124-83-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Na₂S*9H₂O / acetone; H₂O

2: DCC

3: N₂H₄ / tetrahydrofuran

With sodium sulfide; dicyclohexyl-carbodiimide; hydrazine; In tetrahydrofuran; water; acetone;

DOI:10.1021/ja00852a044

Reference yield:

(6R)-7t-(2-carboxy-benzoylamino)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester (55151-65-0) → p-nitrobenzyl ester of 7-aminodeacetoxycephalosporanic acid (29124-83-2)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC

2: N₂H₄ / tetrahydrofuran

With dicyclohexyl-carbodiimide; hydrazine; In tetrahydrofuran;

DOI:10.1021/ja00852a044

upstream raw materials:

(6R)-7t-diethoxyphosphorylamino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(6R)-3-methyl-8-oxo-7t-(3-oxo-3H-isobenzofuran-1-ylideneamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(6R)-7t-amino-3-methylene-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid 4-nitro-benzyl ester; hydrochloride

(6R)-3-methyl-8-oxo-7t-phthalimido-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Downstream raw materials:

p-nitrobenzyl 7-(1H-2-benzopyran-1-onyl-4-carboxamido)-3-methylceph-3-eme-4-carboxylate

p-nitrobenzyl 7-(2-methyl-1-<2H>isoquinolinonyl-4-carboxamido)-3-methylceph-3-eme-4-carboxylate

(6R,7R)-7-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(S)-2-{[(6R,7R)-7-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyl]-amino}-3-phenyl-propionic acid tert-butyl ester

Refernces