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CAS No.: | 96034-64-9 |
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Name: | Side chain for meropenem |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C15H19N3O5S |
Molecular Weight: | 353.399 |
Synonyms: | DMP;(2S,4S) -2-(dimethylaminocarbonyl)-4-mercapto-1- (p-nitrobenzyloxycarbonyl) -1-pyrrolidine;Meropenem Side Chain;(2S,4S)-2-Dimethylaminocarbonyl-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-pyrrolidine;Side chain for meropenem(2S-CIS);2-Dimethylcarbamoyl-4-mercapto-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester;(2s-cis)-2-[(dimethylamino)carbonyl]-4-mercapto-1-pyrrolidinecarboxylic acid (4-nitrophenyl) methyl ester;(2s,4s)-2-(dimethylaminocarbonyl)-4-mercapto-1-(4'-nitrobenzyloxycarbonyl)-1-pyrrolidine;2s,4s)-2-dimethylaminocarbonyl-4-mercapto-1-p-nitrobenzyloxycabonyl-pyrrolidine; |
EINECS: | 619-190-7 |
Density: | 1.36 g/cm3 |
Melting Point: | 117.0 to 121.0 °C |
Boiling Point: | 555.8 °C at 760 mmHg |
Flash Point: | 289.9 °C |
Appearance: | White crystalline solid |
PSA: | 134.47000 |
LogP: | 2.15340 |
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-carboxy-4-mercaptopyrrolidine
N,N-dimethylammonium chloride
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
Conditions | Yield |
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Stage #1: (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-carboxy-4-mercaptopyrrolidine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 5℃; for 0.166667h; Stage #2: N,N-dimethylammonium chloride In N,N-dimethyl-formamide at 0 - 5℃; for 3h; Concentration; | 92.3% |
Stage #1: (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-carboxy-4-mercaptopyrrolidine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 5℃; for 0.166667h; Stage #2: N,N-dimethylammonium chloride In N,N-dimethyl-formamide at 0 - 5℃; for 3h; | 92.3% |
N,N-dimethylammonium chloride
(2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
Conditions | Yield |
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With triethylamine In tetrahydrofuran for 5h; Ambient temperature; | 92% |
bi[(2S,4S)-2-dimethylaminocarbonyl-1-PNZ-pyrrolindin-4-yl]disulfide
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
Conditions | Yield |
---|---|
With tributylphosphine; water In tetrahydrofuran for 0.5h; | 90% |
With tributylphosphine In tetrahydrofuran; water for 0.5h; | 90% |
4-Nitrobenzyl (2S,4S)-4-(acetylthio)-2-[(dimethylamino)carbonyl]pyrrolidine-1-carboxylate
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
Conditions | Yield |
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With acetyl chloride In methanol at 25 - 30℃; for 6h; | 80% |
With methanol; acetyl chloride at 25℃; for 2.5 - 5h; Product distribution / selectivity; Heating / reflux; | 70% |
With Lewatit K 2649 - ion exchange resin In methanol at 25 - 67℃; Product distribution / selectivity; |
(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
Conditions | Yield |
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Multi-step reaction with 4 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 View Scheme |
4-nitrobenzyl chloroformate
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
Conditions | Yield |
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Multi-step reaction with 5 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 View Scheme |
4R-4-hydroxyproline
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 View Scheme | |
Multi-step reaction with 4 steps 1.1: tributylphosphine / tetrahydrofuran / 25 h / 60 - 65 °C 2.1: diethylamino-sulfur trifluoride / 1,2-dichloro-ethane / 26 h / 0 - 60 °C 3.1: sodium carbonate / acetone; water / 5 h / 0 - 50 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 0 - 5 °C 4.2: 3 h / 0 - 5 °C View Scheme |
(2S,4R)-1-p-Nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-hydroxypyrrolidine
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 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 View Scheme |
(2S,4R)-2-dimethylaminocarbonyl-4-mesyloxy-1-p-nitrobenzyloxycarbonylpyrrolidine
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 70 - 80 °C 2.1: sodium hydroxide; water / methanol / 5 - 10 °C 2.2: pH 2 View Scheme |
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: diethylamino-sulfur trifluoride / ethylenediamine / 26 h / 0 - 60 °C 2.1: sodium carbonate / acetone; water / 0.25 h / 0 - 25 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 0 - 5 °C 3.2: 3 h / 0 - 5 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: diethylamino-sulfur trifluoride / 1,2-dichloro-ethane / 26 h / 0 - 60 °C 2.1: sodium carbonate / acetone; water / 5 h / 0 - 50 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 0 - 5 °C 3.2: 3 h / 0 - 5 °C View Scheme |
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Molecular Structure of Side chain for Meropenem (CAS NO.96034-64-9):
IUPAC Name: 3-chloro-10-methylacridin-9-one
Empirical Formula: C15H19N3O5S
Molecular Weight: 353.3935
H bond acceptors: 8
H bond donors: 0
Freely Rotating Bonds: 6
Molar Refractivity: 89.96 cm3
Molar Volume: 258.9 cm3
Surface Tension: 61.1 dyne/cm
Index of Refraction: 1.611
Surface Tension: 61.1 dyne/cm
Density: 1.36 g/cm3
Flash Point: 289.9 °C
Enthalpy of Vaporization: 83.72 kJ/mol
Boiling Point: 555.8 °C at 760 mmHg
Vapour Pressure: 2.17E-12 mmHg at 25°C
Appearance:White Crystalline Solid
Product Categories: Chemical intermediate for Meropenem; intermediatesofmeropenam; Organic acids; API intermediates;(intermediate of meropenem); (the sidechain of meropenem); Intermediates & Fine Chemicals; Pharmaceuticals; Pharmaceutical; pharmaceutical intermediates
Synonyms of Side chain for Meropenem (CAS NO.96034-64-9): 2-Dimethylcarbamoyl-4-mercapto-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester ; (2s-cis)-2-[(dimethylamino)carbonyl]-4-mercapto-1-pyrrolidinecarboxylic acid (4-nitrophenyl) methyl ester ; (2s,4s)-2-(dimethylaminocarbonyl)-4-mercapto-1-(4'-nitrobenzyloxycarbonyl)-1-pyrrolidine ; (2s,4s)-2-dimethylaminocarbonyl-4-mercapto-1-p-nitrobenzyloxycabonyl-pyrrolidine ; (2s,4s)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidine ; side chain for meropenem ; (2s,4s)-2-(dimethylaminocarbonyl)-4-mercapto-1- (p-nitrobenzyloxycarbonyl)-1- py ; (2s,4s)-2-dimethylcarbamoyl-4-mercapto-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester
Side chain for Meropenem (CAS NO.96034-64-9) is a white Crystalline Solid, Side chain for Meropenem (96034-64-9) is an intermediate used for the synthesis of Meropenem.