diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino>-3-cephem-4-carboxylate

Base Information

• Chemical Name: diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino>-3-cephem-4-carboxylate
• CAS No.: 158743-75-0
• Molecular Formula: C₃₄H₃₆N₄O₆S₂
• Molecular Weight: 660.815
• Mol file: 158743-75-0.mol

Synonyms:

Chemical Property of diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino>-3-cephem-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino>-3-cephem-4-carboxylate

There total 4 articles about diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino>-3-cephem-4-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:

tert-butyl (2E)-2-[(tert-butoxycarbonyl)inimo]-4-(2-ethoxy-2-oxoethyl)-1,3-thiazole-3-(2H)-carboxylate (86978-09-8) → diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino>-3-cephem-4-carboxylate (158743-75-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 15percent n-BuLi/n-hexane / tetrahydrofuran / -55 °C

2: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature

3: 82 percent / 2N NaOH / ethanol / 60 °C

4: 1.) TEA, methanesulfonyl chloride, 2.) TEA / 1.) CH₂Cl₂, -60 deg C, 3 h, 2.) CH₂Cl₂, -60 deg C, 2 h

With sodium hydroxide; n-butyllithium; hexane; TEA; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; ethanol; benzene;

DOI:10.7164/antibiotics.47.453

Reference yield:

2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-3-tert-butoxycarbonyloxy-4-methyl-pentanoic acid ethyl ester (1027167-78-7) → diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino>-3-cephem-4-carboxylate (158743-75-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature

2: 82 percent / 2N NaOH / ethanol / 60 °C

3: 1.) TEA, methanesulfonyl chloride, 2.) TEA / 1.) CH₂Cl₂, -60 deg C, 3 h, 2.) CH₂Cl₂, -60 deg C, 2 h

With sodium hydroxide; TEA; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; benzene;

DOI:10.7164/antibiotics.47.453

Reference yield:

(Z)-2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-methyl-pent-2-enoic acid ethyl ester (158743-39-6) → diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino>-3-cephem-4-carboxylate (158743-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 2N NaOH / ethanol / 60 °C

2: 1.) TEA, methanesulfonyl chloride, 2.) TEA / 1.) CH₂Cl₂, -60 deg C, 3 h, 2.) CH₂Cl₂, -60 deg C, 2 h

With sodium hydroxide; TEA; methanesulfonyl chloride; In ethanol;

DOI:10.7164/antibiotics.47.453

upstream raw materials:

diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

(Z)-2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-methyl-pent-2-enoic acid

tert-butyl (2E)-2-[(tert-butoxycarbonyl)inimo]-4-(2-ethoxy-2-oxoethyl)-1,3-thiazole-3-(2H)-carboxylate

2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-3-tert-butoxycarbonyloxy-4-methyl-pentanoic acid ethyl ester