p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate
meropenem
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; hydrogen In tetrahydrofuran; water at 40℃; under 13446.2 Torr; for 1.16667h; Pressure; Temperature; Reagent/catalyst; | 85% |
With formaldehyd; sodium isooctanoate; 5%-palladium/activated carbon In water at 7℃; for 2.5h; Reagent/catalyst; Temperature; | 85.3% |
With platinum on carbon; hydrogen; p-toluidine In tetrahydrofuran at 25℃; under 13501.4 Torr; for 0.683333h; Reagent/catalyst; Solvent; Sealed tube; | 84% |
meropenem
Conditions | Yield |
---|---|
Stage #1: (1R,5R,6S)-6-[(1R)-1-hydroxymethyl]-2-diphenylphosphoryloxocarbapen-2-em-3-carboxylic acid p-nitrobenzyl ester; (2R,4S)-4-dimethylaminomercapto-2-formyl-1-p-nitrobenzyl carbonylpyrrolidine at -5℃; Stage #2: With 5%-palladium/activated carbon; hydrogen at 25℃; Reagent/catalyst; | 44% |
4-nitrobenzyl (4R,5S,6S)-3-[[(3S,5S)-5-(dimethylcarbamoyl)-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxy-ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
meropenem
Conditions | Yield |
---|---|
With 4-methyl-morpholine; hydrogen; acetic acid In water; ethyl acetate at 20 - 25℃; for 3h; pH=~ 7; Product distribution / selectivity; Aqueous buffer; |
Conditions | Yield |
---|---|
Stage #1: 4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at -50 - 25℃; for 1h; Stage #2: With 4-methyl-morpholine; hydrogen; acetic acid; 5%-palladium/activated carbon In water; ethyl acetate; N,N-dimethyl-formamide at 20 - 25℃; for 3h; pH=~ 7; |
meropenem
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran; water at 25 - 30℃; for 2 - 3h; |
(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
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
meropenem
Conditions | Yield |
---|---|
Stage #1: (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; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one; water at -20 - -5℃; Stage #2: With 4-methyl-morpholine; hydrogenchloride; 5% Pd(II)/C(eggshell); hydrogen In 1-methyl-pyrrolidin-2-one; water at 25℃; pH=6.5 - 7; | |
Stage #1: (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; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at -20 - -5℃; Stage #2: With hydrogen; 5%-palladium/activated carbon In 1-methyl-pyrrolidin-2-one at 25℃; pH=6.5 - 7; N-methylmorpholine - hydrochloric acid - buffer; | |
Stage #1: (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; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 0 - 5℃; for 5h; Stage #2: With potassium dihydrogenphosphate; zinc In water; ethyl acetate at 25 - 35℃; for 1h; | |
Stage #1: (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; (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine With N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE at 0 - 5℃; for 5h; Stage #2: With hydrogenchloride In water; ethyl acetate Stage #3: With potassium dihydrogenphosphate In water; ethyl acetate at 25 - 35℃; for 1h; |
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: dmap / dichloromethane / 3 h / 20 - 30 °C 2.1: dichloromethane / 3 h / 20 - 45 °C / Reflux 3.1: triethylamine; 4-toluenesulfonyl azide / dichloromethane / 2 h / 20 - 30 °C 4.1: hydrogenchloride; methanol / dichloromethane; water / 3 h / 20 - 30 °C 5.1: dichloromethane; Isopropyl acetate / 25 - 30 °C 6.1: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux 7.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C 8.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -20 - -5 °C 8.2: 25 °C / pH 6.5 - 7 / N-methylmorpholine - hydrochloric acid - buffer View Scheme |
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: dichloromethane / 3 h / 20 - 45 °C / Reflux 2.1: triethylamine; 4-toluenesulfonyl azide / dichloromethane / 2 h / 20 - 30 °C 3.1: hydrogenchloride; methanol / dichloromethane; water / 3 h / 20 - 30 °C 4.1: dichloromethane; Isopropyl acetate / 25 - 30 °C 5.1: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux 6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C 7.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -20 - -5 °C 7.2: 25 °C / pH 6.5 - 7 / N-methylmorpholine - hydrochloric acid - buffer View Scheme |
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: triethylamine; 4-toluenesulfonyl azide / dichloromethane / 2 h / 20 - 30 °C 2.1: hydrogenchloride; methanol / dichloromethane; water / 3 h / 20 - 30 °C 3.1: dichloromethane; Isopropyl acetate / 25 - 30 °C 4.1: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux 5.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C 6.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -20 - -5 °C 6.2: 25 °C / pH 6.5 - 7 / N-methylmorpholine - hydrochloric acid - buffer View Scheme |
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: hydrogenchloride; methanol / dichloromethane; water / 3 h / 20 - 30 °C 2.1: dichloromethane; Isopropyl acetate / 25 - 30 °C 3.1: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C 5.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -20 - -5 °C 5.2: 25 °C / pH 6.5 - 7 / N-methylmorpholine - hydrochloric acid - buffer View Scheme |
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: dichloromethane; Isopropyl acetate / 25 - 30 °C 2.1: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux 3.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C 4.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -20 - -5 °C 4.2: 25 °C / pH 6.5 - 7 / N-methylmorpholine - hydrochloric acid - buffer View Scheme |
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux 2.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C 3.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -20 - -5 °C 3.2: 25 °C / pH 6.5 - 7 / N-methylmorpholine - hydrochloric acid - buffer View Scheme |
(γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: rhodium (II) octanoate dimer / dichloromethane / 7 h / Reflux 2: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / -35 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / -35 - -30 °C 4: hydrogen; 2,6-dimethylpyridine / palladium 10% on activated carbon / water; tetrahydrofuran / 20 - 25 °C / 13501.4 Torr View Scheme | |
Multi-step reaction with 4 steps 1: rhodium (II) octanoate dimer / acetone / Reflux 2: N-ethyl-N,N-diisopropylamine; zinc(II) iodide / acetone / -30 °C 3: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 4: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme |
4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / -35 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / -35 - -30 °C 3: hydrogen; 2,6-dimethylpyridine / palladium 10% on activated carbon / water; tetrahydrofuran / 20 - 25 °C / 13501.4 Torr View Scheme | |
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; zinc(II) iodide / acetone / -30 °C 2: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 3: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme |
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / -35 - -30 °C 2: hydrogen; 2,6-dimethylpyridine / palladium 10% on activated carbon / water; tetrahydrofuran / 20 - 25 °C / 13501.4 Torr View Scheme | |
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / -35 - -30 °C 2: hydrogen; 2,6-dimethylpyridine / palladium 10% on activated carbon / dichloromethane; water; tetrahydrofuran / 20 - 25 °C / 13501.4 Torr View Scheme |
(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: triethylamine; isopropyl chloroformate / dichloromethane / -30 - -20 °C 2.1: triethylamine / dichloromethane / -20 °C 3.1: N,N-dimethyl-formamide / 70 - 80 °C 4.1: sodium hydroxide; water / methanol / 5 - 10 °C 4.2: pH 2 5.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 6.1: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme |
4R-4-hydroxyproline
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: sodium hydroxide / water / 0 - 5 °C 1.2: 0 - 5 °C 1.3: 0 - 5 °C 2.1: triethylamine; isopropyl chloroformate / dichloromethane / -30 - -20 °C 3.1: triethylamine / dichloromethane / -20 °C 4.1: N,N-dimethyl-formamide / 70 - 80 °C 5.1: sodium hydroxide; water / methanol / 5 - 10 °C 5.2: pH 2 6.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 7.1: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme |
(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: hydrogenchloride; water / ethyl acetate 2: triethylamine / ethyl acetate; toluene 3: rhodium (II) octanoate dimer / acetone / Reflux 4: N-ethyl-N,N-diisopropylamine; zinc(II) iodide / acetone / -30 °C 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 6: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme |
(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 1,1'-carbonyldiimidazole / acetonitrile 2: hydrogenchloride; water / ethyl acetate 3: triethylamine / ethyl acetate; toluene 4: rhodium (II) octanoate dimer / acetone / Reflux 5: N-ethyl-N,N-diisopropylamine; zinc(II) iodide / acetone / -30 °C 6: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 7: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme |
(2S,4R)-1-p-Nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-hydroxypyrrolidine
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / -20 °C 2.1: N,N-dimethyl-formamide / 70 - 80 °C 3.1: sodium hydroxide; water / methanol / 5 - 10 °C 3.2: pH 2 4.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 5.1: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme |
4-Nitrobenzyl (2S,4S)-4-(acetylthio)-2-[(dimethylamino)carbonyl]pyrrolidine-1-carboxylate
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / methanol / 5 - 10 °C 1.2: pH 2 2.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 3.1: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme |
(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: triethylamine / ethyl acetate; toluene 2: rhodium (II) octanoate dimer / acetone / Reflux 3: N-ethyl-N,N-diisopropylamine; zinc(II) iodide / acetone / -30 °C 4: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 5: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme |
(2S,4R)-2-dimethylaminocarbonyl-4-mesyloxy-1-p-nitrobenzyloxycarbonylpyrrolidine
meropenem
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide / 70 - 80 °C 2.1: sodium hydroxide; water / methanol / 5 - 10 °C 2.2: pH 2 3.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 4.1: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme |
1-[(S)-benzosuber-1-yloxycarbonyloxy]ethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
A
carbon dioxide
B
1-benzosuberol
C
acetaldehyde
D
meropenem
Conditions | Yield |
---|---|
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; pH=7.4; Mechanism; Reagent/catalyst; pH-value; Time; |
indan-2-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
A
formaldehyd
B
indan-2-ol
C
carbon dioxide
D
meropenem
Conditions | Yield |
---|---|
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; for 2h; pH=7.4; Mechanism; Reagent/catalyst; pH-value; Time; |
tetral-2-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
A
formaldehyd
B
carbon dioxide
C
1,2,3,4-tetrahydronaphthalen-2 ol
D
meropenem
Conditions | Yield |
---|---|
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; for 2h; pH=7.4; Mechanism; Reagent/catalyst; pH-value; Time; |
benzosuber-2-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
A
formaldehyd
B
carbon dioxide
C
3,4-benzo-3-cyclohepten-1-ol
D
meropenem
Conditions | Yield |
---|---|
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; for 2h; pH=7.4; Mechanism; Reagent/catalyst; pH-value; Time; |
Conditions | Yield |
---|---|
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; for 2h; pH=7.4; Mechanism; Reagent/catalyst; pH-value; Time; |
(S)-indan-1-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
A
formaldehyd
B
carbon dioxide
C
1-Indanol
D
meropenem
Conditions | Yield |
---|---|
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; pH=7.4; Mechanism; Time; |
(R)-indan-1-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
A
formaldehyd
B
carbon dioxide
C
1-Indanol
D
meropenem
Conditions | Yield |
---|---|
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; pH=7.4; Mechanism; Time; |
[(S)-benzosuber-1-yl] iodomethyl carbonate
meropenem
(S)-benzosuber-1-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: [(S)-benzosuber-1-yl] iodomethyl carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; | 84% |
iodomethyl (R)-tetral-1-yl carbonate
meropenem
(R)-tetral-1-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: iodomethyl (R)-tetral-1-yl carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; | 82% |
iodomethyl tetral-2-yl carbonate
meropenem
tetral-2-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: iodomethyl tetral-2-yl carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; | 82% |
(R)-benzosuber-1-yl iodomethyl carbonate
meropenem
(R)-benzosuber-1-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: (R)-benzosuber-1-yl iodomethyl carbonate | 79% |
(S)-indan-1-yl iodomethyl carbonate
meropenem
(S)-indan-1-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: (S)-indan-1-yl iodomethyl carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; | 75% |
(R)-indan-1-yl iodomethyl carbonate
meropenem
(R)-indan-1-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: (R)-indan-1-yl iodomethyl carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; | 72% |
indan-2-yl iodomethyl carbonate
meropenem
indan-2-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: indan-2-yl iodomethyl carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; | 71% |
benzosuber-2-yl iodomethyl carbonate
meropenem
benzosuber-2-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: benzosuber-2-yl iodomethyl carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; | 65% |
1-iodoethyl isopropyl carbonate
meropenem
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: 1-iodoethyl isopropyl carbonate In N,N-dimethyl-formamide at 0℃; for 0.5h; Reagent/catalyst; Concentration; Time; | 64% |
[(S)-benzosuber-1-yl] iodomethyl carbonate
acetic anhydride
meropenem
(S)-benzosuber-1-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-1-acetyl-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: acetic anhydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #3: [(S)-benzosuber-1-yl] iodomethyl carbonate In N,N-dimethyl-formamide at 0℃; for 1h; | 62% |
iodomethyl (S)-tetral-1-yl carbonate
meropenem
(S)-tetral-1-yloxycarbonyloxymethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: iodomethyl (S)-tetral-1-yl carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; | 57% |
Conditions | Yield |
---|---|
With triethylamine In methanol at 0 - 20℃; for 1h; | 50% |
[(1S)-benzosuber-1-yl] 1-iodoethyl carbonate
meropenem
1-[(S)-benzosuber-1-yloxycarbonyloxy]ethyl (1R,5S,6S)-2-{[(3S,5S)-5-(N,N-dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: meropenem With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: [(1S)-benzosuber-1-yl] 1-iodoethyl carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; | 43% |
Conditions | Yield |
---|---|
With triethylamine In dimethyl sulfoxide at 20℃; | 16.3% |
iodomethylbenzoate
meropenem
benzoic acid 4-nitrophenoxycarbonyloxymethyl ester
Conditions | Yield |
---|---|
Stage #1: meropenem; benzoic acid 4-nitrophenoxycarbonyloxymethyl ester In N,N-dimethyl-formamide for 1h; Stage #2: iodomethylbenzoate With sodium carbonate In N,N-dimethyl-formamide for 1h; | 14% |
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; water at 25℃; Rate constant; Kinetics; var. pH from 4.0 to 8.0, var. temp., var. buffers; |
D-cysteine
meropenem
Conditions | Yield |
---|---|
With Hepps buffer at 37℃; pH=8.4; Kinetics; |
L-Cysteine
meropenem
Conditions | Yield |
---|---|
With Hepps buffer at 37℃; pH=8.4; Kinetics; Further Variations:; pH-values; Temperatures; | |
With sodium hydroxide at 20℃; for 3h; pH=7; Substitution; ring cleavage; |
L-homocysteine
meropenem
Conditions | Yield |
---|---|
With Hepps buffer at 37℃; pH=8.4; Kinetics; |
cysteinylglycine
meropenem
Conditions | Yield |
---|---|
With Hepps buffer at 37℃; pH=8.4; Kinetics; |
GLUTATHIONE
meropenem
Conditions | Yield |
---|---|
With Hepps buffer at 37℃; pH=8.4; Kinetics; |
L-Cysteine isopropyl ester
meropenem
Conditions | Yield |
---|---|
With Hepps buffer at 37℃; pH=8.4; Kinetics; |
Cysteamine
meropenem
Conditions | Yield |
---|---|
With Hepps buffer at 37℃; pH=8.4; Kinetics; |
meropenem
Conditions | Yield |
---|---|
With Hepps buffer at 37℃; pH=8.4; Kinetics; Hydrolysis; |
Conditions | Yield |
---|---|
In water-d2 at 25℃; Equilibrium constant; Carboxylation; |
1. Introduction of Meropenem
Meropenem is one kind of white or almost white crystalline powder. The IUPAC name of this chemical is (4R,5S,6S)-3-[(3S,5S)-5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid. Besides, Meropenem belongs to Active Pharmaceutical Ingredients;Antibacterial;Cnbio;pharmaceutical intermediates. In addition, Meropenem Classification Code is Anti-Bacterial Agents; Anti-Infective Agents; Drug / Therapeutic Agent; Reproductive Effect. What's more, Meropenem is soluble in 5% monobasic potassium phosphate solution, sparingly soluble in water, very slightly soluble in hydrated ethanol.
Meropenem (CAS NO.96036-03-2) was originally developed by Sumitomo Pharmaceuticals. It is marketed outside Japan by AstraZeneca with the brand names Merrem and Meronem . Other brand names include Mepem (Taiwan) , Meropen (Japan, Korea) and Neopenem (India) . It gained FDA approval in July 1996. It penetrates well into many tissues and body fluids including the cerebrospinal fluid, bile, heart valves, lung, and peritoneal fluid.
2. Properties of Meropenem
Physical properties about Meropenem are:
(1)Index of Refraction: 1.639; (2)Surface Tension: 68.4 dyne/cm; (3)Density: 1.42 g/cm3; (4)Flash Point: 333.2 °C; (5)Enthalpy of Vaporization: 106.42 kJ/mol; (6)Boiling Point: 627.4 °C at 760 mmHg; (7)Vapour Pressure: 2.27E-18 mmHg at 25 °C; (8)log Kow = -1.25 (est); (9)XLogP3-AA: -2.4; (10)H-Bond Donor: 3; (11)H-Bond Acceptor: 7.
3. Structure Descriptors of Meropenem
(1)InChI: InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
(2)InChIKey: DMJNNHOOLUXYBV-PQTSNVLCSA-N
(3)Canonical SMILES : CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)N(C)C)C(=O)O)C(C)O
(4)Isomeric SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)N(C)C)C(=O)O)[C@@H](C)O
(5)Smiles: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)N(C)C)C(=O)O)[C@@H](C)O
4. Toxicity of Meropenem
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | intravenous | 2gm/kg (2000mg/kg) | LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Chemotherapy Vol. 40(Suppl, |
mouse | LD50 | intravenous | 2650mg/kg (2650mg/kg) | BEHAVIORAL: ATAXIA BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Chemotherapy Vol. 40(Suppl, |
mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | Chemotherapy Vol. 40(Suppl, | |
mouse | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Chemotherapy Vol. 40(Suppl, | |
rat | LD50 | intravenous | 2850mg/kg (2850mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Chemotherapy Vol. 40(Suppl, |
rat | LD50 | oral | > 5gm/kg (5000mg/kg) | Chemotherapy Vol. 40(Suppl, | |
rat | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Chemotherapy Vol. 40(Suppl, |
5. Safety Information of Meropenem
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
6. Uses of Meropenem
Meropenem (CAS NO.96036-03-2) is an ultra-broad spectrum injectable antibiotic used to treat a wide variety of infections, including meningitis and pneumonia. It is a beta-lactam and belongs to the subgroup of carbapenem, similar to imipenem and ertapenem.
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View