diphenylmethyl (6R,7R)-7-[2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetamido]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

Chemical Name:diphenylmethyl (6R,7R)-7-[2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetamido]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
CAS No.:307002-27-3
Molecular Formula:C₃₈H₃₆Cl₃N₃O₇S₂
Molecular Weight:817.211
Hs Code.:

diphenylmethyl (6R,7R)-7-[2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetamido]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Synonyms:diphenylmethyl (6R,7R)-7-[2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetamido]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

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Chemical Property of diphenylmethyl (6R,7R)-7-[2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetamido]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

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Technology Process of diphenylmethyl (6R,7R)-7-[2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetamido]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 15 articles about diphenylmethyl (6R,7R)-7-[2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetamido]-3-(chloromethyl)-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: 81.0%

: 307002-20-6
2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetic acid

: 208512-82-7
(6R,7R)-7-{2-[4-((E)-2-tert-Butoxycarbonyl-vinyl)-2,5-dichloro-phenylsulfanyl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

: 307002-27-3
diphenylmethyl (6R,7R)-7-[2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetamido]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:: With dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/S0968-0896(02)00336-X

Reference yield:

: C₁₇H₁₈Cl₃NO₄S

: 79349-53-4
(6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxyli acid diphenylmethyl ester hydrochloride

: 307002-27-3
diphenylmethyl (6R,7R)-7-[2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetamido]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:: With potassium hydrogencarbonate; In tetrahydrofuran; water; at 19 - 25 ℃; for 1h; pH=7.5 - 8.2; Large scale;

Reference yield:

: 7145-82-6
2,4,5-trichloroiodobenzene

: 307002-27-3
diphenylmethyl (6R,7R)-7-[2-({4-[(1E)-2-{[2-(tert-butoxy)-2-oxoethyl]carbamoyl}eth-1-en-1-yl]-2,5-dichlorophenyl}sulfanyl)acetamido]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / Pd(OAc)3; PPh₃; Bu₃N / dimethylformamide / 3 h / 80 °C

2: 75 percent / dimethylformamide / 1 h / 20 °C

3: 79 percent / TFA / CH₂Cl₂; methoxybenzene / 1 h / 20 °C

4: dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / 20 °C

5: 10.4 g / N-methylmorpholine / dimethylformamide / 1 h / 0 - 20 °C

6: 80 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

7: 81 percent / dicyclohecylcarbodiimide / tetrahydrofuran; CH₂Cl₂ / 2 h / 20 °C

With 4-methyl-morpholine; sodium hydroxide; palladium(III) acetate; tributyl-amine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; methoxybenzene; N,N-dimethyl-formamide; 1: Heck reaction;
DOI:10.1016/S0968-0896(02)00336-X