Product Name

  • Name

    Tebipenem

  • EINECS
  • CAS No. 161715-21-5
  • Article Data9
  • CAS DataBase
  • Density 1.75
  • Solubility
  • Melting Point
  • Formula C16H21N3O4S2
  • Boiling Point 624.5±65.0 °C(Predicted)
  • Molecular Weight 383.492
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 161715-21-5 (Tebipenem)
  • Hazard Symbols
  • 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);;
  • PSA 144.04000
  • LogP -0.02830

Synthetic route

(+)-(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
161715-20-4

(+)-(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

(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
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%
C19H25N3O4S2

C19H25N3O4S2

(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
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 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)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyl 4-nitrobenzoate

(4R,5S,6S)-3-((1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyl 4-nitrobenzoate

(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
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 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
179337-62-3

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
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
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
161715-27-1

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
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
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
161715-28-2

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

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

(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
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
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,5R,6S)-3-((diphenoxyphosphoryl)oxy)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyl p-nitrobenzoate

(4R,5R,6S)-3-((diphenoxyphosphoryl)oxy)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyl p-nitrobenzoate

(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
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
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
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

(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
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
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
C11H15NO5

C11H15NO5

3-mercapto-1-(1,3-thiazolin-2-yl)azetidine hydrochloride

3-mercapto-1-(1,3-thiazolin-2-yl)azetidine hydrochloride

(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
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
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.
(+)-(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

(+)-(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

(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
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
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 0 °C
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 1 h / 30 °C
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
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

iodomethyl pivaloate
53064-79-2

iodomethyl pivaloate

L-084

L-084

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide for 0.5h; Large scale;91.9%
With potassium carbonate In acetonitrile at 20℃;
Stage #1: (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 With caesium carbonate In N,N-dimethyl-formamide for 0.5h; Inert atmosphere;
Stage #2: iodomethyl pivaloate In N,N-dimethyl-formamide for 1h;
(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
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

Chloromethyl pivalate
18997-19-8

Chloromethyl pivalate

L-084

L-084

Conditions
ConditionsYield
Stage #1: (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 With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 25℃; for 1h;
Stage #2: Chloromethyl pivalate In water at 25℃; for 0.166667h;		89.7%
With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 4h;78%
Stage #1: Chloromethyl pivalate With potassium iodide In N,N-dimethyl-formamide at 60℃; for 3h;
Stage #2: (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 With triethylbenzylammonium iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 8h; Reagent/catalyst;		61%
Stage #1: (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 With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 1h; Large scale;
Stage #2: Chloromethyl pivalate In N,N-dimethyl-formamide at 45℃; for 5h; Large scale;		1.05 kg
(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
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

Chloromethyl pivalate
18997-19-8

Chloromethyl pivalate

C22H31N3O6S2*ClH

C22H31N3O6S2*ClH

Conditions
ConditionsYield
Stage #1: (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; Chloromethyl pivalate With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 35℃; for 1h;
Stage #2: With hydrogenchloride In water at 7 - 8℃; Time;		89.1%
(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
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

1-methyl-cyclohexanecarboxylic acid chloromethyl ester

1-methyl-cyclohexanecarboxylic acid chloromethyl 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 1-methyl-cyclohexanecarbonyloxymethyl 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 1-methyl-cyclohexanecarbonyloxymethyl ester

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 4h;88%
(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
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

3-chloro-1(3H)-isobenzofuranone
6295-21-2

3-chloro-1(3H)-isobenzofuranone

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

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
With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 4h;84%
(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
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

4-methylbenzoic acid chloromethyl ester
70190-61-3

4-methylbenzoic acid chloromethyl 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

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
With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 4h;84%
(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
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

1-chloroethyl cyclohexyl carbonate
99464-83-2

1-chloroethyl cyclohexyl carbonate

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 1-cyclohexyloxycarbonyloxy-ethyl 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 1-cyclohexyloxycarbonyloxy-ethyl ester

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 4h;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
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

chloromethyl p-chlorobenzoate
41657-97-0

chloromethyl p-chlorobenzoate

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

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
With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 4h;81%
(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
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

4-methyl-cyclohexanecarboxylic acid chloromethyl ester

4-methyl-cyclohexanecarboxylic acid chloromethyl 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-cyclohexanecarbonyloxymethyl 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-cyclohexanecarbonyloxymethyl ester

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 4h;80%
(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
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

chloromethyl 2-cyclohexylacetate

chloromethyl 2-cyclohexylacetate

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 cyclohexylacetoxymethyl 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 cyclohexylacetoxymethyl ester

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 4h;76%
(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
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

chloromethyl cyclohexanoic acid ester
29916-48-1

chloromethyl cyclohexanoic acid 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 cyclohexanecarbonyloxymethyl 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 cyclohexanecarbonyloxymethyl ester

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 4h;71%
(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
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

C28H43N3O9S2

C28H43N3O9S2

C44H62N6O12S4

C44H62N6O12S4

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 10h;66%
(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
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

4-chloromethyl-5-methyl-1,3-dioxol-2-one
80841-78-7

4-chloromethyl-5-methyl-1,3-dioxol-2-one

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

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
With N-benzyl-N,N,N-triethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 4h;54%

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