CAS No.96034-64-9,Side chain for meropenem Suppliers

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Basic Information

Molecular Structure:
CAS No.:	96034-64-9
Name:	Side chain for meropenem
Article Data:	11

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

Synthetic route

: 127966-47-6
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-carboxy-4-mercaptopyrrolidine

: 506-59-2
N,N-dimethylammonium chloride

: 96034-64-9
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Conditions

Conditions	Yield
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%

: 506-59-2
N,N-dimethylammonium chloride

: 151072-00-3
(2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one

: 96034-64-9
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 5h; Ambient temperature;	92%

: 936226-36-7
bi[(2S,4S)-2-dimethylaminocarbonyl-1-PNZ-pyrrolindin-4-yl]disulfide

: 96034-64-9
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Conditions

Conditions	Yield
With tributylphosphine; water In tetrahydrofuran for 0.5h;	90%
With tributylphosphine In tetrahydrofuran; water for 0.5h;	90%

: 96034-61-6
4-Nitrobenzyl (2S,4S)-4-(acetylthio)-2-[(dimethylamino)carbonyl]pyrrolidine-1-carboxylate

: 96034-64-9
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Conditions

Conditions	Yield
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;

: 96034-57-0
(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid

: 96034-64-9
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Conditions

Conditions	Yield
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

: 4457-32-3
4-nitrobenzyl chloroformate

: 96034-64-9
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Conditions

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

: 51-35-4
4R-4-hydroxyproline

: 96034-64-9
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Conditions

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

: 130625-69-3
(2S,4R)-1-p-Nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-hydroxypyrrolidine

: 96034-64-9
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Conditions

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

: 130625-70-6
(2S,4R)-2-dimethylaminocarbonyl-4-mesyloxy-1-p-nitrobenzyloxycarbonylpyrrolidine

: 96034-64-9
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Conditions

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,4R)-2-carboxy-4-(3-fluorophenylthio)pyrrolidine

: 96034-64-9
(2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine

Conditions

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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Chemistry

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

Specification

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.

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