(6R)-7t-benzylideneamino-3-methyl-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)-7t-benzylideneamino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• CAS No.: 36954-81-1
• Molecular Formula: C₁₉H₂₂N₂O₃S
• Molecular Weight: 358.461
• Mol file: 36954-81-1.mol

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

Chemical Property of (6R)-7t-benzylideneamino-3-methyl-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)-7t-benzylideneamino-3-methyl-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)-7t-benzylideneamino-3-methyl-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:

3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) + benzaldehyde (100-52-7) + isobutene (115-11-7,15220-85-6) → (6R)-7t-benzylideneamino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (36954-81-1)

Guidance literature:

Multistep reaction; (i) H₂SO₄, dioxane, (ii) /BRN= 471223/, benzene;

DOI:10.1021/jo00942a008

Reference yield:

(6R)-7t-benzylideneamino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (36954-81-1) → (6R)-3,7c-dimethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (32956-88-0)

Guidance literature:

Multi-step reaction with 4 steps

1: KOtBu / -30 °C

2: TsOH / ethyl acetate; H₂O / Ambient temperature

3: Et₃N / CHCl₃

4: CF₃CO₂H / Ambient temperature

With potassium tert-butylate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In chloroform; water; ethyl acetate;

DOI:10.1021/jo00942a008

Reference yield:

(6R)-7t-benzylideneamino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (36954-81-1) → (6R)-3,7c-dimethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (32860-50-7)

Guidance literature:

Multi-step reaction with 3 steps

1: KOtBu / -30 °C

2: TsOH / ethyl acetate; H₂O / Ambient temperature

3: Et₃N / CHCl₃

With potassium tert-butylate; toluene-4-sulfonic acid; triethylamine; In chloroform; water; ethyl acetate;

DOI:10.1021/jo00942a008

upstream raw materials:

3-deacetyloxy-7-aminocephalosporanic acid

benzaldehyde

isobutene

Downstream raw materials:

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

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

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

(6R)-3,7t-dimethyl-8-oxo-7c-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester