(6R)-3-methyl-7t-(2-nitro-benzene(Ξ)sulfinylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (6R)-3-methyl-7t-(2-nitro-benzene(Ξ)sulfinylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• CAS No.: 64394-81-6
• Molecular Formula: C₁₈H₂₁N₃O₆S₂
• Molecular Weight: 439.513
• Mol file: 64394-81-6.mol

Synonyms:

Chemical Property of (6R)-3-methyl-7t-(2-nitro-benzene(Ξ)sulfinylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R)-3-methyl-7t-(2-nitro-benzene(Ξ)sulfinylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

There total 1 articles about (6R)-3-methyl-7t-(2-nitro-benzene(Ξ)sulfinylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl 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:

t-butyl 7α-amino-3-methyl-3-cephem-4-carboxylate (33610-06-9) + ortho-nitrophenylsulfinyl chloride (36828-02-1) → (6R)-3-methyl-7t-(2-nitro-benzene(Ξ)sulfinylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (64394-81-6,64470-25-3,73464-80-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1248/cpb.27.2727

Reference yield:

(6R)-3-methyl-7t-(2-nitro-benzene(Ξ)sulfinylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (64394-81-6,64470-25-3,73464-80-9) → (6R)-3-methyl-7t-(4-nitro-benzene(Ξ)sulfinylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (65269-27-4)

Guidance literature:

Multi-step reaction with 4 steps

1: (i) quinoline, CHCl₃, (ii) SOCl₂

2: NaBH₄ / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C

3: KI, aq. Na₂S₂O₃ / CH₂Cl₂; methanol; acetic acid

4: Et₃N / tetrahydrofuran

With sodium tetrahydroborate; sodium thiosulfate; triethylamine; potassium iodide; In tetrahydrofuran; methanol; dichloromethane; acetic acid; dimethyl sulfoxide;

DOI:10.1248/cpb.27.2727

Reference yield:

(6R)-3-methyl-7t-(2-nitro-benzene(Ξ)sulfinylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (64394-81-6,64470-25-3,73464-80-9) → (R)-3-methyl-7-(4-nitro-phenylsulfanylimino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (64394-78-1)

Guidance literature:

Multi-step reaction with 5 steps

1: (i) quinoline, CHCl₃, (ii) SOCl₂

2: NaBH₄ / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C

3: KI, aq. Na₂S₂O₃ / CH₂Cl₂; methanol; acetic acid

4: Et₃N / tetrahydrofuran

5: Et₃N, SOCl₂ / CH₂Cl₂

With sodium tetrahydroborate; thionyl chloride; sodium thiosulfate; triethylamine; potassium iodide; In tetrahydrofuran; methanol; dichloromethane; acetic acid; dimethyl sulfoxide;

DOI:10.1248/cpb.27.2727

upstream raw materials:

t-butyl 7α-amino-3-methyl-3-cephem-4-carboxylate

ortho-nitrophenylsulfinyl chloride

Downstream raw materials:

(R)-3-methyl-7-(2-nitro-phenylsulfanylimino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

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

(6R)-3-methyl-7c-(2-nitro-phenylsulfanylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

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