3-[4-(2-tert-butoxycarbonylamino-ethylsulfanylmethyl)-[1,2,3]thiadiazol-5-ylsulfanyl]-7-[2-(6-tert-butoxycarbonylamino-pyridin-2-yl)-2-trityloxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: 3-[4-(2-tert-butoxycarbonylamino-ethylsulfanylmethyl)-[1,2,3]thiadiazol-5-ylsulfanyl]-7-[2-(6-tert-butoxycarbonylamino-pyridin-2-yl)-2-trityloxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 259533-24-9
• Molecular Formula: C₆₁H₆₀N₈O₉S₄
• Molecular Weight: 1177.46
• Mol file: 259533-24-9.mol

Synonyms:

Chemical Property of 3-[4-(2-tert-butoxycarbonylamino-ethylsulfanylmethyl)-[1,2,3]thiadiazol-5-ylsulfanyl]-7-[2-(6-tert-butoxycarbonylamino-pyridin-2-yl)-2-trityloxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[4-(2-tert-butoxycarbonylamino-ethylsulfanylmethyl)-[1,2,3]thiadiazol-5-ylsulfanyl]-7-[2-(6-tert-butoxycarbonylamino-pyridin-2-yl)-2-trityloxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 10 articles about 3-[4-(2-tert-butoxycarbonylamino-ethylsulfanylmethyl)-[1,2,3]thiadiazol-5-ylsulfanyl]-7-[2-(6-tert-butoxycarbonylamino-pyridin-2-yl)-2-trityloxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl 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: 45.0%

(Z)-2-(2-tert-butoxycarbonylaminopyrid-6-yl)-2-(triphenylmethoxyimino)acetic acid (258497-18-6) + (6R,7R)-7-Amino-3-[4-(2-tert-butoxycarbonylamino-ethylsulfanylmethyl)-[1,2,3]thiadiazol-5-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester; compound with toluene-4-sulfonic acid → 3-[4-(2-tert-butoxycarbonylamino-ethylsulfanylmethyl)-[1,2,3]thiadiazol-5-ylsulfanyl]-7-[2-(6-tert-butoxycarbonylamino-pyridin-2-yl)-2-trityloxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (259533-24-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran;

DOI:10.1016/S0960-894X(00)00603-X

Reference yield:

Pyridine-2,6-dicarboxylic acid (499-83-2) → 3-[4-(2-tert-butoxycarbonylamino-ethylsulfanylmethyl)-[1,2,3]thiadiazol-5-ylsulfanyl]-7-[2-(6-tert-butoxycarbonylamino-pyridin-2-yl)-2-trityloxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (259533-24-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 45 percent / (PhO)2PON₃; TEA

2: POCl₃ / dimethylformamide; ethyl acetate

3: 65 percent / NaH / dimethylformamide

4: 85 percent / (CF₃CO)2O; pyridine / CH₂Cl₂

5: 40 percent / NaBO₃; AcOH

6: 100 percent / NH₂OH; pyridine / ethanol

7: TEA

8: 92 percent / aq. NaOH / propan-2-ol

9: 45 percent / POCl₃; Huenig's base / tetrahydrofuran

With pyridine; sodium perborate; sodium hydroxide; TEA; diphenyl phosphoryl azide; hydroxylamine; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; 1: Curtius rearrangement / 5: Pummerer rearrangement;

DOI:10.1016/S0960-894X(00)00603-X

Reference yield:

methyl 6-tert-butoxycarbonylamino-2-pyridinecarboxylate (258497-48-2) → 3-[4-(2-tert-butoxycarbonylamino-ethylsulfanylmethyl)-[1,2,3]thiadiazol-5-ylsulfanyl]-7-[2-(6-tert-butoxycarbonylamino-pyridin-2-yl)-2-trityloxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (259533-24-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 65 percent / NaH / dimethylformamide

2: 85 percent / (CF₃CO)2O; pyridine / CH₂Cl₂

3: 40 percent / NaBO₃; AcOH

4: 100 percent / NH₂OH; pyridine / ethanol

5: TEA

6: 92 percent / aq. NaOH / propan-2-ol

7: 45 percent / POCl₃; Huenig's base / tetrahydrofuran

With pyridine; sodium perborate; sodium hydroxide; TEA; hydroxylamine; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; 2: Pummerer rearrangement;

DOI:10.1016/S0960-894X(00)00603-X

upstream raw materials:

(Z)-2-(2-tert-butoxycarbonylaminopyrid-6-yl)-2-(triphenylmethoxyimino)acetic acid

Pyridine-2,6-dicarboxylic acid

methyl 6-tert-butoxycarbonylamino-2-pyridinecarboxylate

6-[(tert-butoxycarbonyl)amino]-2-pyridinecarboxylic acid