p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-(3,4-dihydroxyphenyl)thiazol-4-yl>-3-cephem-4-carboxylate

Base Information

Chemical Name:p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-(3,4-dihydroxyphenyl)thiazol-4-yl>-3-cephem-4-carboxylate
CAS No.:159267-55-7
Molecular Formula:C₂₉H₂₈N₄O₉S
Molecular Weight:608.629
Hs Code.:

Synonyms:p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-(3,4-dihydroxyphenyl)thiazol-4-yl>-3-cephem-4-carboxylate

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Chemical Property of p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-(3,4-dihydroxyphenyl)thiazol-4-yl>-3-cephem-4-carboxylate

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Technology Process of p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-(3,4-dihydroxyphenyl)thiazol-4-yl>-3-cephem-4-carboxylate

There total 7 articles about p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-(3,4-dihydroxyphenyl)thiazol-4-yl>-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: 91.0%

: 138038-57-0
3,4-dihydroxybenzothioamide

: 138038-53-6
p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-(2-bromomethylcarbonyl)-3-cephem-4-carboxylate

: 159267-55-7
p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-(3,4-dihydroxyphenyl)thiazol-4-yl>-3-cephem-4-carboxylate

Guidance literature:: In 1,1,2-trichloroethane; isopropyl alcohol; at 65 ℃; for 3h;
DOI:10.7164/antibiotics.47.1052

Reference yield:

: 108493-71-6
p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

: 159267-55-7
p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-(3,4-dihydroxyphenyl)thiazol-4-yl>-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / LiCl / dichloropalladium(II) diacetonitrilate / dimethylformamide / 1 h / Ambient temperature

2: 1.0M Br₂, 2,6-lutidine / CH₂Cl₂; CCl₄

3: 91 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

4: 87 percent / 1.0M LiOH / tetrahydrofuran / 0.5 h / ultrasonic irradiation

5: 100 percent / H₂O, AcOH / acetonitrile / 2 h

6: 91 percent / propan-2-ol; 1,1,2-trichloro-ethane / 3 h / 65 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; water; bromine; acetic acid; lithium chloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; tetrachloromethane; dichloromethane; 1,1,2-trichloroethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;
DOI:10.7164/antibiotics.47.1052

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 159267-55-7
p-nitrobenzyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-(3,4-dihydroxyphenyl)thiazol-4-yl>-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

2: 87 percent / 1.0M LiOH / tetrahydrofuran / 0.5 h / ultrasonic irradiation

3: 100 percent / H₂O, AcOH / acetonitrile / 2 h

4: 91 percent / propan-2-ol; 1,1,2-trichloro-ethane / 3 h / 65 °C

With dmap; lithium hydroxide; water; acetic acid; In tetrahydrofuran; dichloromethane; 1,1,2-trichloroethane; isopropyl alcohol; acetonitrile;
DOI:10.7164/antibiotics.47.1052