Products Categories
CAS No.: | 161715-21-5 |
---|---|
Name: | Tebipenem |
Article Data: | 9 |
Molecular Structure: | |
Formula: | C16H21N3O4S2 |
Molecular Weight: | 383.492 |
Synonyms: | (1R,5S,6S)-6-(1(R)-Hydroxyethyl)-1-methyl-2-(1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl)-1-carba-2-penem-3-carboxylic acid;;UNII-Q2TWQ1I31U;;1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid,3-((1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl)thio)-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-,(4R,5S,6S);; |
Density: | 1.75 |
Boiling Point: | 624.5±65.0 °C(Predicted) |
PSA: | 144.04000 |
LogP: | -0.02830 |
(+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-{[1-(2-thiazolin-2-yl)-3-azetidinyl]mercapto}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid p-nitrobenzyl ester
(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With hydrogen In water; butan-1-ol at 20℃; under 15001.5 Torr; for 4h; Solvent; Pressure; Reagent/catalyst; | 94.5% |
With 0.5% Pd/C; hydrogen; sodium hydrogencarbonate In water; butan-1-ol at 25 - 30℃; under 7500.75 Torr; for 3h; Reagent/catalyst; | 89.3% |
With sodium hydrogencarbonate; palladium on activated charcoal In water; butan-1-ol at 20℃; under 3000.24 Torr; for 1.5h; | 82% |
(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate In water at 13℃; under 11251.1 Torr; for 2.5h; Large scale; | 78.9% |
(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate In water; butan-1-ol at 20℃; under 3000.3 - 3750.38 Torr; for 7h; Solvent; Pressure; Temperature; | 77% |
With 2,6-dimethylpyridine; palladium 10% on activated carbon; hydrogen In water at 20℃; under 13501.4 Torr; for 4.5h; Reagent/catalyst; Pressure; Temperature; Time; Large scale; | 75.7% |
3-methanesulfonyloxy-1-(1,3-thiazolin-2-yl)azetidine
(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 88 percent / potassium thioacetate / dimethylformamide / 5.5 h / 100 °C 2.1: KOH / propan-2-ol; methanol / 0.17 h / 5 °C 2.2: 87 percent / HCl / propan-2-ol; methanol / 15 h / 5 °C 3.1: 94 percent / diisopropyl ethylamine; MeCN / 2 h / -20 °C 4.1: 82 percent / sodium hydrogen carbonate / Pd-C / butan-1-ol; H2O / 1.5 h / 20 °C / 3000.24 Torr View Scheme |
1-(1,3-thiazolin-2-yl-)azetidin-3-ol
(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 93 percent / DMAP; Et3N / tetrahydrofuran / 0.5 h / 5 °C 2.1: 88 percent / potassium thioacetate / dimethylformamide / 5.5 h / 100 °C 3.1: KOH / propan-2-ol; methanol / 0.17 h / 5 °C 3.2: 87 percent / HCl / propan-2-ol; methanol / 15 h / 5 °C 4.1: 94 percent / diisopropyl ethylamine; MeCN / 2 h / -20 °C 5.1: 82 percent / sodium hydrogen carbonate / Pd-C / butan-1-ol; H2O / 1.5 h / 20 °C / 3000.24 Torr View Scheme |
3-acetylthio-1-(1,3-thiazolin-2-yl)azetidine
(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: KOH / propan-2-ol; methanol / 0.17 h / 5 °C 1.2: 87 percent / HCl / propan-2-ol; methanol / 15 h / 5 °C 2.1: 94 percent / diisopropyl ethylamine; MeCN / 2 h / -20 °C 3.1: 82 percent / sodium hydrogen carbonate / Pd-C / butan-1-ol; H2O / 1.5 h / 20 °C / 3000.24 Torr View Scheme |
(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 94 percent / diisopropyl ethylamine; MeCN / 2 h / -20 °C 2: 82 percent / sodium hydrogen carbonate / Pd-C / butan-1-ol; H2O / 1.5 h / 20 °C / 3000.24 Torr View Scheme | |
Multi-step reaction with 2 steps 1.1: acetonitrile / 0.17 h / 20 °C 1.2: 10 h / -20 °C 2.1: hydrogen; sodium hydrogencarbonate; palladium 10% on activated carbon / butan-1-ol; water / 7 h / 20 °C / 3000.3 - 3750.38 Torr View Scheme | |
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 3.5 h / -20 °C 2: 0.5% Pd/C; sodium hydrogencarbonate; hydrogen / butan-1-ol; water / 3 h / 25 - 30 °C / 7500.75 Torr View Scheme | |
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile 2: hydrogen; water; palladium on activated charcoal / butan-1-ol View Scheme |
(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: acetonitrile / 0.17 h / 20 °C 1.2: 10 h / -20 °C 2.1: hydrogen; sodium hydrogencarbonate; palladium 10% on activated carbon / butan-1-ol; water / 7 h / 20 °C / 3000.3 - 3750.38 Torr View Scheme |
(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 3.5 h / -20 °C 2: 0.5% Pd/C; sodium hydrogencarbonate; hydrogen / butan-1-ol; water / 3 h / 25 - 30 °C / 7500.75 Torr View Scheme | |
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile 2: hydrogen; water; palladium on activated charcoal / butan-1-ol View Scheme |
(4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: C11H15NO5; 3-mercapto-1-(1,3-thiazolin-2-yl)azetidine hydrochloride In 1,2-dichloro-ethane at -10℃; for 3h; 2-supported perfluorosulfonic acid resin pyridinium salt; Stage #2: 3-mercapto-1-(1,3-thiazolin-2-yl)azetidine hydrochloride With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 5℃; for 6h; Reagent/catalyst; | 58.5 %Chromat. |