90776-59-3

Basic information

• Product Name: beta-Methyl vinyl phosphate (MAP)
• Synonyms: p-nitrobenzyl (1r,5r,6s)-6-[(1r)-1-hydroxyethyl]-2-;P-NITROBENZYL (1R,5R,6S)-6-[(1R)-1-HYDROXYETHYL]-2-[(DIPHENYLPHOSPHONO)OXY]-1-METHYLCARBAPEN-2-EM-3-CARBOXYLATE;P-NITROBENZYL (1R,5R,6S)-6-[(1R)-HYDROXY ETHYL]-2-[(DIPHENYLPHOSPHONO)OXY]-1-METHYL CARBAPEN-2EM-3-CARBOXYLATE;3-(DIPHENOXY-PHOSPHORYLOXY)-6-(1-HYDROXY-ETHYL)-4-METHYL-7-OXO-1-AZA-BICYCLO[3.2.0]HEPT-2-ENE-2-CARBOXYLIC ACID 4-NITRO-BENZYL ESTER;(4r,5s,6s)-3-(diphenyloxy)phosphoryloxy-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate;4-NITROBENZYL (1R,5R,6S)-6-[(1R)-1-HYDROXYETHYL]-2-[(DIPHENYLPHOSPHONO)OXY]-1-METHYLCARBAPEN-2-EM-3-CARBOXYLATE;4-NITROBENZYL-(1R,5R,6S)-6-[(1R)-1-HYDROXYETHYL]-2-[(DIPHENYLPHOSPHONO)OXY]-1-METHYLCARBAPEN-2-EM-3-CARBOXYLIC ACID;beta-Methyl vinyl phosphate (MAP)
• CAS NO: 90776-59-3
• Molecular Formula: C₂₉H₂₇N₂O₁₀P
• Molecular Weight: 594.51
• EINECS: 1308068-626-2
• Product Categories: API intermediates;pharmaceutical intermediates;other Products;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Phosphorylating and Phosphitylating Agents
• Mol File: 90776-59-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 129-131?C
• Boiling Point: 722.363 °C at 760 mmHg
• Flash Point: 390.671 °C
• Appearance: White or off-white powder
• Density: 1.47 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.653
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.36±0.20(Predicted)
• CAS DataBase Reference: beta-Methyl vinyl phosphate (MAP)(CAS DataBase Reference)
• NIST Chemistry Reference: beta-Methyl vinyl phosphate (MAP)(90776-59-3)
• EPA Substance Registry System: beta-Methyl vinyl phosphate (MAP)(90776-59-3)

Safety Data

• Hazardous Substances Data: 90776-59-3(Hazardous Substances Data)

Usage

Description

A chemical compound.

Uses

Meropenem intermediate. A 1β-methyl carbapenem derivative as antibacterial agent.

storage

-20°C Freezer, Under Inert Atmosphere

InChI:InChI=1/C29H27N2O10P/c1-18-25-24(19(2)32)28(33)30(25)26(29(34)38-17-20-13-15-21(16-14-20)31(35)36)27(18)41-42(37,39-22-9-5-3-6-10-22)40-23-11-7-4-8-12-23/h3-16,18-19,24-25,32H,17H2,1-2H3/t18-,19-,24-,25-/m1/s1

Upstream product

• 90822-25-6 p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate 
• 1499-21-4 Diphenylphosphinic chloride 
• 90822-23-4 (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 90822-22-3 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one 
• 90822-24-5 (γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester 
• 105995-50-4 magnesium 4-nitrobenzyl malonate 
• 77359-11-6 propanedioic acid mono[(4-nitrophenyl)methyl] ester 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 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 
• 101765-69-9 (S)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thiopropionic acid S-phenyl ester 
• 86978-81-6 Acetic acid (2R,3R)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester 
• 90776-58-2 (S)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid 
• 83973-55-1 (2R,4S,5R,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 

Downstream Products

• 206117-20-6 (4R,5S,6S)-3-[(3S,5S)-5-Difluoromethylsulfanylmethyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 155485-28-2 (2S,4S,3'S)-4-[(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-2-(4-nitro-benzyloxycarbonyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-1'-methyl-[2,3']bipyrrolidinyl-1-carboxylic acid 4-nitro-benzyl ester 
• 206117-22-8 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-[(3S,5S)-1-(4-nitro-benzyloxycarbonyl)-5-(pyridin-4-ylsulfanylmethyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 138324-78-4 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-[(3S,5S)-1-(4-nitro-benzyloxycarbonyl)-5-(pyridin-3-ylsulfanylmethyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 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 
• 120410-24-4 biapenem 
• 120764-68-3 p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate 
• 101135-08-4 (4S,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 101151-51-3 (4R,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 97033-03-9 (4R,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 466652-14-2 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(3S,5S)-5-(3-isopropyl-thiazolidin-2-yl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 466651-83-2 p-nitrobenzyl(1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-2-[(S)-5-((R)-4-hydroxymethylthiazolidin-2-yl)-1-(p-nitrobenzyloxycarbonyl)-pyrrolidin-(S)-3-ylthio]-1-methyl-1-carbapen-2-em-3-carboxylate 
• 466652-16-4 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(3S,5S)-5-(3-methanesulfonyl-thiazolidin-2-yl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 153836-85-2 4-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate 

Relevant articles and documents

AN IMPROVED PROCESS FOR THE PREPARATION OF MEROPENEM

The present invention provides an improved process for the preparation of methyl carbapenem derivative of formula (I) or its pharmaceutically acceptable salts or hydrates thereof in a pure form.

PROCESS FOR THE PREPARATION OF CARBAPENEM COMPOUNDS

The present invention relates to a process for the preparation of carbapenem compound of Formula (I), wherein P1 is hydrogen or a carboxyl protecting group, P3 is hydrogen or a hydroxyl protecting group, R1 is C1-3 alkyl, and A is selected from a group consisting of a) Formula (II), b) Formula (III), c) Formula (IV), d) Formula (V), e) Formula (VI), f) Formula (VII), wherein P2 is hydrogen or an amino protecting group, R2 and R3 may be same or different and are hydrogen, C1-5 alkyl, optionally substituted aryl, or optionally substituted heteroaryl, and X1 is O or S, or its stereoisomers, or salts thereof.

IMPROVED METHOD FOR THE CRYSTALLIZATION OF INTERMEDIATES OF CARBAPENEM ANTIBIOTICS

The present invention relates to an azetidinone compound extremely useful as a common intermediate for the synthesis of 1β-methylcarbapenem compounds. The present invention provides a crystallization method to obtain a crystal which has a higher quality and a higher stability than a conventional crystal and is excellent in filterability at the time of recovering crystal; an azetidinone compound having a low content of impurity; and an azetidinone compound which has a controlled particle size distribution of crystals and improved handleability and stability. The crystallization is carried out by adding a hydrocarbon solvent to a solution in which an azetidinone compound extremely useful as a common intermediate for the synthesis of 1β-methylcarbapenem compounds is dissolved in the presence of a seed crystal in an amount of 200% by weight or less based on the weight of the azetidinone compound. According to the method, the crystal having a high quality and a high stability and excellent filterability at the time of recovering the crystal can be obtained.