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161715-20-4
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Basic Information
CAS No.: 161715-20-4
Name: 4-Nitrobenzyl(1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-Methyl-2-[1-(1,3-thiazolin-2-yl)azetidin -3-yl]thio-1-carbapen-2-eM-3-carboxylate
Molecular Structure:
Molecular Structure of 161715-20-4 (4-Nitrobenzyl(1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-Methyl-2-[1-(1,3-thiazolin-2-yl)azetidin -3-yl]thio-1-carbapen-2-eM-3-carboxylate)
Formula: C23H26N4O6S2
Molecular Weight: 518.615
Synonyms: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, [4R-[4α,5β,6β(R*)]]-;Tebipenem Condensation Compound;
Density: 1.63±0.1 g/cm3 (20 oC 760 Torr), Calc.*
Boiling Point: 741.4±70.0 °C(Predicted)
Solubility: Very slightly soluble (0.1 g/L) (25 oC), Calc.*
PSA: 178.86000
LogP: 2.06190
Related products
Synthetic route
93711-81-0, 90776-59-3

(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

1-(4,5-dihydro-1,3-thiazol-2-yl)-3-mercaptoazetidine hydrochloride

161715-20-4

(+)-(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

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; acetonitrile at -20℃; for 2h;94%
With N-ethyl-N,N-diisopropylamine at -20℃; for 3.5h; Temperature;88.5%
With N-ethyl-N,N-diisopropylamine In acetonitrile
179337-62-3

3-methanesulfonyloxy-1-(1,3-thiazolin-2-yl)azetidine

161715-20-4

(+)-(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

Conditions
ConditionsYield
Multi-step reaction with 3 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
View Scheme
161715-27-1

1-(1,3-thiazolin-2-yl-)azetidin-3-ol

161715-20-4

(+)-(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

Conditions
ConditionsYield
Multi-step reaction with 4 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
View Scheme
161715-28-2

3-acetylthio-1-(1,3-thiazolin-2-yl)azetidine

161715-20-4

(+)-(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

Conditions
ConditionsYield
Multi-step reaction with 2 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
View Scheme

(+)-(4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-(diphenylphosphoryloxy)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid p-nitrobenzyl ester

1-(4,5-dihydro-1,3-thiazol-2-yl)-3-mercaptoazetidine hydrochloride

161715-20-4

(+)-(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

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0℃; for 4h;
161715-20-4

(+)-(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

161715-21-5

(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
ConditionsYield
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%
161715-20-4

(+)-(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

3-[1-(4,5-dihydro-thiazol-2-yl)-azetidin-3-ylsulfanyl]-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / sodium hydrogen carbonate / Pd-C / butan-1-ol; H2O / 1.5 h / 20 °C / 3000.24 Torr
2: 54 percent / benzyltriethylammonium chloride; diisopropylethylamine / dimethylformamide / 4 h / 45 °C
View Scheme
161715-20-4

(+)-(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

3-[1-(4,5-dihydro-thiazol-2-yl)-azetidin-3-ylsulfanyl]-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 3-oxo-1,3-dihydro-isobenzofuran-1-yl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / sodium hydrogen carbonate / Pd-C / butan-1-ol; H2O / 1.5 h / 20 °C / 3000.24 Torr
2: 84 percent / benzyltriethylammonium chloride; diisopropylethylamine / dimethylformamide / 4 h / 45 °C
View Scheme
161715-20-4

(+)-(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

3-[1-(4,5-dihydro-thiazol-2-yl)-azetidin-3-ylsulfanyl]-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methyl-benzoyloxymethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / sodium hydrogen carbonate / Pd-C / butan-1-ol; H2O / 1.5 h / 20 °C / 3000.24 Torr
2: 84 percent / benzyltriethylammonium chloride; diisopropylethylamine / dimethylformamide / 4 h / 45 °C
View Scheme
161715-20-4

(+)-(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

3-[1-(4,5-dihydro-thiazol-2-yl)-azetidin-3-ylsulfanyl]-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-chloro-benzoyloxymethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / sodium hydrogen carbonate / Pd-C / butan-1-ol; H2O / 1.5 h / 20 °C / 3000.24 Torr
2: 81 percent / benzyltriethylammonium chloride; diisopropylethylamine / dimethylformamide / 4 h / 45 °C
View Scheme
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