trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate

Base Information

• Chemical Name: trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate
• CAS No.: 138976-46-2
• Molecular Formula: C₂₁H₂₁Cl₃N₄O₅S₃
• Molecular Weight: 611.979
• Mol file: 138976-46-2.mol

Synonyms:trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate

Chemical Property of trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate

There total 6 articles about trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-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: 16.96%

trichloroethyl 2α-(chloromethyl)-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate (104641-33-0) + 2-mercapto-5-methyl-1,3,4-thiadiazole (29490-19-5) → trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate (138976-46-2)

Guidance literature:

In acetone; 1.) 60 deg C, 1 h, 2.) RT, 24 h; pH 6.8;

DOI:10.1016/0223-5234(91)90005-8

Reference yield:

trichloroethyl 2β-(chloromethyl)-2α-methyl-6β-(N-nitrosophenoxyacetamido)-penam-3α-carboxylate (138976-41-7) → trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate (138976-46-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 98.7 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 °C

2: 90 percent / H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / 310.4 Torr

3: 46.7 percent / toluene / 0.33 h / Heating

4: 30.3 percent / PBr₃ / dimethylformamide / 1.75 h / 0 °C

5: 16.96 percent / acetone / 1.) 60 deg C, 1 h, 2.) RT, 24 h; pH 6.8

With hydrogen; phosphorus tribromide; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/0223-5234(91)90005-8

Reference yield:

trichloroethyl 2β-(chloromethyl)-2α-methyl-6β-(N-nitrosophenoxyacetamido)-penam-3α-carboxylate 1R-oxide (138976-42-8) → trichloroethyl 2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate (138976-46-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / 310.4 Torr

2: 46.7 percent / toluene / 0.33 h / Heating

3: 30.3 percent / PBr₃ / dimethylformamide / 1.75 h / 0 °C

4: 16.96 percent / acetone / 1.) 60 deg C, 1 h, 2.) RT, 24 h; pH 6.8

With hydrogen; phosphorus tribromide; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/0223-5234(91)90005-8

upstream raw materials:

trichloroethyl 2α-(chloromethyl)-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylate

2-mercapto-5-methyl-1,3,4-thiadiazole

trichloroethyl 2β-(chloromethyl)-2α-methyl-6β-(N-nitrosophenoxyacetamido)-penam-3α-carboxylate

trichloroethyl 2β-(chloromethyl)-2α-methyl-6β-(N-nitrosophenoxyacetamido)-penam-3α-carboxylate 1R-oxide

Downstream raw materials:

2α-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-2β-methyl-6β-(phenoxyacetamido)-penam-3α-carboxylic acid