151072-00-3

Basic information

• Product Name: (2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one
• Synonyms: (2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one
• CAS NO: 151072-00-3
• Molecular Weight: 308.315
• Mol File: 151072-00-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 543.8±50.0 °C(Predicted)
• Density: 1.523±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one(151072-00-3)
• EPA Substance Registry System: (2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one(151072-00-3)

Safety Data

• Hazardous Substances Data: 151072-00-3(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyclo<2.2.1>heptan-3-one" is a complex molecule with a bicyclic structure. It contains a thia and azabicyclo components, as well as a p-nitrobenzyloxycarbonyl group. The compound has a molecular formula of C14H14N2O4S and a molecular weight of 310.34 g/mol. It is commonly used as a building block in organic synthesis and medicinal chemistry research, and its specific stereochemistry and functional groups make it a valuable intermediate in the preparation of various pharmaceuticals and bioactive compounds.

Upstream product

• 96034-57-0 (2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 151071-99-7 (2S,4R)-1-p-nitrobenzyloxycarbonyl-4-methanesulfonyloxy-2-pyrrolidinethiocarboxylic acid 
• 4457-32-3 4-nitrobenzyl chloroformate 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 138508-10-8 1-<(2S,4S)-4-mercapto-1-p-nitrobenzyloxycarbonyl-2-pyrrolidinylcarbonyl>-4-methylpiperidine 
• 96034-64-9 (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidine 
• 127966-47-6 (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-carboxy-4-mercaptopyrrolidine 
• 1206708-72-6 C₂₂H₂₉N₅O₆S₂ 
• 1350538-24-7 (2S,4S)-2-[(4-aminosulfonylphen-1-yl)iminomethylformyl]-4-thiol-1-(p-nitrobenzyloxycarbonyl)pyrrolidine 
• 1312953-83-5 (4R,5S,6S)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((4-sulfamoylbenzyl)carbamoyl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 
• 1350538-25-8 (4R,5S,6S)-3-[[(3S,5S)-N-(4-nitrobenzyloxycarbonyl)-5-[(4-aminosulfonylphen-1-yl)methyl]carbamoyl]-3-pyrrolidinyl]thio-6-[(R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrobenzyl)methyl ester 
• 202467-69-4 (2S,4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-(4-nitrobenzyl)pyrrolidine carboxylate 

Relevant articles and documents

Preparation method of improved meropenem side chain intermediate thiol lactone by adding surfactant

The invention provides a preparation method of an improved meropenem side chain intermediate thiol lactone by adding a surfactant. The meropenem side chain intermediate is prepared by performing carboxyl activation and hydroxyl activation on M1 [(2S, 4R)-2-carboxyl-1-(4-nitrobenzyloxycarbonyl) pyrrolidine] and adding a cheap surfactant to vulcanize and form a ring by a one-pot method. The surfacetension of dichloromethane and water can be reduced by utilizing the surfactant, wherein the molar weight of the added surfactant is only 3-10% of the molar weight of M1, the highest yield of the obtained thiol lactone reaches 96.5% or above, the purity can reach 98.1% or above, the reaction temperature is increased by adding the surfactant, and when the temperature is controlled to be-16 DEG C to-15 DEG C, the thiol lactone can still be synthesized at a high yield, the surfactant source is wide, meanwhile, after a solvent and water are evaporated and removed, the surfactant can be recycled, so that the environmental pollution is reduced, and the industrial production of the thiol lactone is facilitated.

Preparation method of meropenem side chain intermediate mercaptan lactone

The invention provides a synthesis method of a meropenem side chain intermediate mercaptan lactone with the high yield. The synthesis method comprises the steps that (2S,4R)-2-carboxyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine) is added into dichloromethane, the liquid temperature is kept at minus 26 DEG C to minus 17 DEG C, isopropyl chlorocarbonate is dropwise added, and then triethylamine is dropwise added to activate carboxyl; MsCl is dropwise added under the same temperature condition, and then triethylamine is dropwise added to activate hydroxyl; a sodium sulfide nonahydrate, a phase transfer catalyst and water are dissolved into a solution, and the solution is added into a reaction solution under the same temperature condition; deionized water is added at 0 DEG C for liquid separation, and an organic phase is separated; the organic phase is subjected to a reflux reaction in a water bath kettle; and alkali is used for adjusting till pH is 8 to 9, an oil phase 1 is separated, the oil phase 1 continues to be adjusted through acid till pH is 1 to 2, an oil phase 2 is separated, after the oil phase 2 is subjected to decompression distillation, oily liquid is obtained, a crystallization solvent is added into the oily liquid, then a low-temperature reaction for bath cooling is conducted, and filtering is conducted to obtain the meropenem side chain intermediate mercaptan lactone.

Meropenem side chain intermediate and preparation method thereof

The invention relates to a meropenem side chain intermediate and a preparation method thereof. The preparation method is used for preparing a (1S, 4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyalo[2, 2, 1]heptan-3-one (shown in the formula and called as thiollactone for short). In a nitrogen protective atmosphere, (2S, 4R)-2-carboxyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine is added into dichloromethane, the mixture undergoes a carboxyl activation reaction, the reaction product undergoes a hydroxy acylation reaction, the reaction product undergoes a sulfuration cyclization reaction, the reaction product is subjected to reduced pressure distillation, a crystallization solvent is added into the distillation product, the product is cooled to a temperature of -5 to -10 DEG C and precipitates for 2h, and the crystals are filtered to form the (1S, 4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicyalo[2, 2, 1]heptan-3-one (shown in the formula and called as thiollactone for short). The preparation method provides high purity thiollactone. A high-purity meropenem side chain can be prepared through thiollactone aminolysis. The preparation method utilizes mild reaction conditions, is safe, does not produce pollution on the environment and is suitable for industrial production. The thiollactone can be used for synthesis of an ertapenem side chain, a doripenem side chain and some amino-compounds, esters and ketones.