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96036-03-2

Basic Information
CAS No.: 96036-03-2
Name: Meropenem
Molecular Structure:
Molecular Structure of 96036-03-2 (Meropenem)
Formula: C17H25N3O5S
Molecular Weight: 383.46
Synonyms: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid,3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-,(4R,5S,6S)-;1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid,3-[[5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-,[4R-[3(3S*,5S*),4a,5b,6b(R*)]]-;Antibiotic SM 7338;ICI 194660;Mepem;Meronem;Meropen;Merrem;Merrem IV;SM 7338;
EINECS: 641-424-1
Density: 1.42 g/cm3
Melting Point:
Boiling Point: 627.4 °C at 760 mmHg
Flash Point: 333.2 °C
Solubility:
Appearance: white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 135.48000
LogP: -0.04130
Synthetic route
96036-02-1

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

96036-03-2

meropenem

Conditions
ConditionsYield
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%

(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

96036-03-2

meropenem

Conditions
ConditionsYield
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%
141818-52-2

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

96036-03-2

meropenem

Conditions
ConditionsYield
With 4-methyl-morpholine; hydrogen; acetic acid In water; ethyl acetate at 20 - 25℃; for 3h; pH=~ 7; Product distribution / selectivity; Aqueous buffer;

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

Conditions
ConditionsYield
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;

(5R,6S,8R,2'S,4'S)-p-nitrobenzyl-3-[4-(1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl)pyrrolidinylthio]-4-methyl-6-(1-hydroxyethyl)-1-azabicyclo[3.2.0]-hept-2-en-7-oxo-2carboxylate

96036-03-2

meropenem

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran; water at 25 - 30℃; for 2 - 3h;
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

96034-64-9

(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

96036-03-2

meropenem

Conditions
ConditionsYield
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;

C19H34N2O4SSi

96036-03-2

meropenem

Conditions
ConditionsYield
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

C17H29N3O3Si

96036-03-2

meropenem

Conditions
ConditionsYield
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

C23H34N2O7Si

96036-03-2

meropenem

Conditions
ConditionsYield
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

C23H32N4O7Si

96036-03-2

meropenem

Conditions
ConditionsYield
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

C17H18N4O7

96036-03-2

meropenem

Conditions
ConditionsYield
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

C3H4N2*C17H18N4O7

96036-03-2

meropenem

Conditions
ConditionsYield
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
90822-24-5

(γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester

96036-03-2

meropenem

Conditions
ConditionsYield
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
104873-15-6

4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate

96036-03-2

meropenem

Conditions
ConditionsYield
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

p-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[(bis(2,4-dichlorophenyl)phosphono)oxy]-1-methylcarbapen-2-em-3-carboxylate

96034-64-9

(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

96036-03-2

meropenem

Conditions
ConditionsYield
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
96034-57-0

(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid

96036-03-2

meropenem

Conditions
ConditionsYield
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
51-35-4

4R-4-hydroxyproline

96036-03-2

meropenem

Conditions
ConditionsYield
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
90822-22-3

(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one

96036-03-2

meropenem

Conditions
ConditionsYield
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
93711-85-4, 97101-07-0, 113033-46-8, 120710-59-0, 120710-60-3, 90776-58-2

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

96036-03-2

meropenem

Conditions
ConditionsYield
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
130625-69-3

(2S,4R)-1-p-Nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-hydroxypyrrolidine

96036-03-2

meropenem

Conditions
ConditionsYield
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
96034-61-6

4-Nitrobenzyl (2S,4S)-4-(acetylthio)-2-[(dimethylamino)carbonyl]pyrrolidine-1-carboxylate

96036-03-2

meropenem

Conditions
ConditionsYield
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
90822-23-4

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one

96036-03-2

meropenem

Conditions
ConditionsYield
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
130625-70-6

(2S,4R)-2-dimethylaminocarbonyl-4-mesyloxy-1-p-nitrobenzyloxycarbonylpyrrolidine

96036-03-2

meropenem

Conditions
ConditionsYield
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
1450666-42-8

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

124-38-9

carbon dioxide

C

75-07-0

acetaldehyde

D

96036-03-2

meropenem

Conditions
ConditionsYield
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; pH=7.4; Mechanism; Reagent/catalyst; pH-value; Time;
1450666-26-8

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

50-00-0

formaldehyd

B

4254-29-9

indan-2-ol

C

124-38-9

carbon dioxide

D

96036-03-2

meropenem

Conditions
ConditionsYield
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; for 2h; pH=7.4; Mechanism; Reagent/catalyst; pH-value; Time;
1450666-27-9

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

50-00-0

formaldehyd

B

124-38-9

carbon dioxide

C

530-91-6

1,2,3,4-tetrahydronaphthalen-2 ol

D

96036-03-2

meropenem

Conditions
ConditionsYield
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; for 2h; pH=7.4; Mechanism; Reagent/catalyst; pH-value; Time;
1450666-28-0

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

50-00-0

formaldehyd

B

124-38-9

carbon dioxide

C

13249-77-9

3,4-benzo-3-cyclohepten-1-ol

D

96036-03-2

meropenem

Conditions
ConditionsYield
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; for 2h; pH=7.4; Mechanism; Reagent/catalyst; pH-value; Time;

1-(isopropoxycarbonyloxy)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

124-38-9

carbon dioxide

B

75-07-0

acetaldehyde

C

67-63-0

isopropyl alcohol

D

96036-03-2

meropenem

Conditions
ConditionsYield
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; for 2h; pH=7.4; Mechanism; Reagent/catalyst; pH-value; Time;
1450666-36-0

(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

50-00-0

formaldehyd

B

124-38-9

carbon dioxide

C

6351-10-6

1-Indanol

D

96036-03-2

meropenem

Conditions
ConditionsYield
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; pH=7.4; Mechanism; Time;
1450666-39-3

(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

50-00-0

formaldehyd

B

124-38-9

carbon dioxide

C

6351-10-6

1-Indanol

D

96036-03-2

meropenem

Conditions
ConditionsYield
With water; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 37℃; pH=7.4; Mechanism; Time;
1450666-33-7

[(S)-benzosuber-1-yl] iodomethyl carbonate

96036-03-2

meropenem

1450666-38-2

(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
ConditionsYield
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%
1450666-32-6

iodomethyl (R)-tetral-1-yl carbonate

96036-03-2

meropenem

1450666-40-6

(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
ConditionsYield
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%
1450666-24-6

iodomethyl tetral-2-yl carbonate

96036-03-2

meropenem

1450666-27-9

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
ConditionsYield
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%
1450666-34-8

(R)-benzosuber-1-yl iodomethyl carbonate

96036-03-2

meropenem

1450666-41-7

(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
ConditionsYield
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%
1450666-29-1

(S)-indan-1-yl iodomethyl carbonate

96036-03-2

meropenem

1450666-36-0

(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
ConditionsYield
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%
1450666-30-4

(R)-indan-1-yl iodomethyl carbonate

96036-03-2

meropenem

1450666-39-3

(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
ConditionsYield
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%
1450666-23-5

indan-2-yl iodomethyl carbonate

96036-03-2

meropenem

1450666-26-8

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
ConditionsYield
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%
1450666-25-7

benzosuber-2-yl iodomethyl carbonate

96036-03-2

meropenem

1450666-28-0

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
ConditionsYield
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%
84089-73-6, 91508-00-8

1-iodoethyl isopropyl carbonate

96036-03-2

meropenem

1-(isopropoxycarbonyloxy)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
ConditionsYield
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%
1450666-33-7

[(S)-benzosuber-1-yl] iodomethyl carbonate

108-24-7

acetic anhydride

96036-03-2

meropenem

1450666-43-9

(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
ConditionsYield
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%
1450666-31-5

iodomethyl (S)-tetral-1-yl carbonate

96036-03-2

meropenem

1450666-37-1

(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
ConditionsYield
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%
55183-45-4

hex-5-in-carboxyl chloride

96036-03-2

meropenem

C23H31N3O6S

Conditions
ConditionsYield
With triethylamine In methanol at 0 - 20℃; for 1h;50%
1450666-35-9

[(1S)-benzosuber-1-yl] 1-iodoethyl carbonate

96036-03-2

meropenem

1450666-42-8

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
ConditionsYield
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%

C21H31N9O5S

96036-03-2

meropenem

C38H56N12O10S2

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20℃;16.3%
13943-33-4

iodomethylbenzoate

96036-03-2

meropenem

170097-82-2

benzoic acid 4-nitrophenoxycarbonyloxymethyl ester

(4R,5S,6S)-3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-1-[[benzoyloxymethoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid benzoyloxymethyl ester

Conditions
ConditionsYield
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%
96036-03-2

meropenem

A

C34H50N6O10S2

B

C34H50N6O10S2

Conditions
ConditionsYield
With potassium dihydrogenphosphate; water at 25℃; Rate constant; Kinetics; var. pH from 4.0 to 8.0, var. temp., var. buffers;
921-01-7

D-cysteine

96036-03-2

meropenem

(4R,5S)-5-[(1R,2R)-1-((S)-1-Carboxy-2-mercapto-ethylcarbamoyl)-2-hydroxy-propyl]-3-((3S,5S)-5-dimethylcarbamoyl-pyrrolidin-3-ylsulfanyl)-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
With Hepps buffer at 37℃; pH=8.4; Kinetics;
52-90-4

L-Cysteine

96036-03-2

meropenem

(4R,5S)-5-[(1R,2R)-1-((R)-1-Carboxy-2-mercapto-ethylcarbamoyl)-2-hydroxy-propyl]-3-((3S,5S)-5-dimethylcarbamoyl-pyrrolidin-3-ylsulfanyl)-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
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;
6027-13-0

L-homocysteine

96036-03-2

meropenem

(4R,5S)-5-[(1R,2R)-1-((S)-1-Carboxy-3-mercapto-propylcarbamoyl)-2-hydroxy-propyl]-3-((3S,5S)-5-dimethylcarbamoyl-pyrrolidin-3-ylsulfanyl)-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
With Hepps buffer at 37℃; pH=8.4; Kinetics;
19246-18-5

cysteinylglycine

96036-03-2

meropenem

(4R,5S)-5-{(1R,2R)-1-[(R)-1-(Carboxymethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-2-hydroxy-propyl}-3-((3S,5S)-5-dimethylcarbamoyl-pyrrolidin-3-ylsulfanyl)-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
With Hepps buffer at 37℃; pH=8.4; Kinetics;
70-18-8

GLUTATHIONE

96036-03-2

meropenem

(4R,5S)-5-((1R,2R)-1-{(S)-1-Carboxy-3-[(R)-1-(carboxymethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-propylcarbamoyl}-2-hydroxy-propyl)-3-((3S,5S)-5-dimethylcarbamoyl-pyrrolidin-3-ylsulfanyl)-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
With Hepps buffer at 37℃; pH=8.4; Kinetics;
79178-11-3

L-Cysteine isopropyl ester

96036-03-2

meropenem

(4R,5S)-3-((3S,5S)-5-Dimethylcarbamoyl-pyrrolidin-3-ylsulfanyl)-5-[(1R,2R)-2-hydroxy-1-((R)-1-isopropoxycarbonyl-2-mercapto-ethylcarbamoyl)-propyl]-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
With Hepps buffer at 37℃; pH=8.4; Kinetics;
60-23-1

Cysteamine

96036-03-2

meropenem

(4R,5S)-3-((3S,5S)-5-Dimethylcarbamoyl-pyrrolidin-3-ylsulfanyl)-5-[(1R,2R)-2-hydroxy-1-(2-mercapto-ethylcarbamoyl)-propyl]-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
With Hepps buffer at 37℃; pH=8.4; Kinetics;
96036-03-2

meropenem

Meropenoic acid

Conditions
ConditionsYield
With Hepps buffer at 37℃; pH=8.4; Kinetics; Hydrolysis;
96036-03-2

meropenem

NaH(13)CO3

NaH(13)CO3

meropenem-CO2 adduct

Conditions
ConditionsYield
In water-d2 at 25℃; Equilibrium constant; Carboxylation;
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Specification

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: IrritantXi
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.