Protected meropenem

Basic Information

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CAS Number

96036-02-1

Molecular Formula

C32H35N5O11S

Molecular Weight

697.71 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Melting Point

150-153 ºC (dec.)

Specific Rotation

14 º (c=1,MeOH)

SMILES

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CC1C2C(C(=O)N2C(=C1SC3CC(N(C3)C(=O)OCC4=CC=C(C=C4)[N+](=O)[O-])C(=O)N(C)C)C(=O)OCC5=CC=C(C=C5)[N+](=O)[O-])C(C)O

InChI

InChI=1S/C32H35N5O11S/c1-17-26-25(18(2)38)30(40)35(26)27(31(41)47-15-19-5-9-21(10-6-19)36(43)44)28(17)49-23-13-24(29(39)33(3)4)34(14-23)32(42)48-16-20-7-11-22(12-8-20)37(45)46/h5-12,17-18,23-26,38H,13-16H2,1-4H3/t17-,18-,23+,24+,25-,26-/m1/s1

InChIKey

PJGGEFUAFDAJJT-ALUDVLAQSA-N

LogP

4.13860

Complexity

1350

Safety Information

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Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

protected meropenem
4-nitrobenzyl (5s,6s)-3-[((3s,5s)-5-[(dimethylamino)carbonyl]-1-{[(4-nitrobenzyl)oxy]carbonyl}pyrrolidinyl)sulfanyl]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Meropenem & Intermediates Protected Meropenem P-NITROBENZYL(4R,5S,6S)-3-[(3S,5S)-(5-DIMETHYLAMINOCARBONYL-1-P-NITROBENZYLOXYCARBONYL)-PYRROLIDIN-3-YLSULFANYL]-6-((R)-1-HYDROXY-ETHYL)-4-METHYL-7-OXO-1-AZA-BICYCLO[3.2.0]HEPT-2ENE-4-CARBOXYLATE
intermediate of meropenem
1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
3-(((3S,5S)-5-((dimet hylamino)carbonyl)-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-(4R,5S,6S)-1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
3-((5-((dimethylamino)carbonyl)-3-pyrrolidinyl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-(4R-(3(S*,5S*)
4-alpha,5-beta,6-beta(R*)))
Antibiotic SM 7338
BRN 6940582
ICI 194660
Meropenem
Meropenem anhydrous
Meropenemum [INN-Latin]
Merrem
SM 7338
Meropenem protected
n-1
(4-nitrophenyl)methyl 3-[5-(dimethylcarbamoyl)-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-2-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
C32H35N5O11S
(4R,5S,6S)-p-nitrobenzyl 3-<(3S,5S)-(5-dimethylaminocarbonyl-1-p-nitrobenzyloxycarbonyl)pyrrolidin-3-yl>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
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
(4-Nitrophenyl)methyl (4R,5S,6S)-3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (ACI)
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[5-[(dimethylamino)carbonyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, [4R-[3(3S*,5S*),4α,5β,6β(R*)]]- (ZCI)
(4R,5S,6S)-(p-Nitrobenzyl) 3-[[(3S,5S)-1-(p-nitrobenzyloxycarbonyl)-5-(dimethylaminocarbonyl)-3-pyrrolidinyl]thio]-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Meropenem bis(p-nitrobenzyl) ester
Meropenem p-nitrobenzyl diester
p-Nitrobenzyl (4R,5S,6S)-3-[[(3S,5S)-1-(p-nitrobenzyloxycarbonyl)-5-(dimethylaminocarbonyl)pyrrolidin-3-yl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Meropenemp-nitrobenzyldiester
SCHEMBL441087
96036-02-1

MDL Number

MFCD08703333

FAQ

What are the physical and chemical properties of Protected meropenem (CAS: 96036-02-1)?

Protected meropenem is a semi-synthetic carbapenem antibiotic with a molecular weight of approximately 545.56 g/mol. It is a white to off-white crystalline powder with limited solubility in water. The compound is known for its stability and reactivity in acidic conditions, making it less susceptible to degradation. It is used in the synthesis of other carbapenem derivatives. For more detailed properties, refer to the material safety data sheet (MSDS).

How is Protected meropenem (CAS: 96036-02-1) typically synthesized?

Protected meropenem is synthesized through a multi-step process involving the preparation of a protected β-lactam ring from a carbamic acid intermediate. Common synthetic routes involve the use of a reducing agent to generate the protected carbapenem structure, followed by various functional group manipulations. The yield and selectivity of the synthesis can vary, but the process typically requires careful control of pH and temperature. For detailed synthesis methods, see reference journals such as Organic Letters or Chemical Communications.

What industries use Protected meropenem (CAS: 96036-02-1)?

Protected meropenem is primarily used in the pharmaceutical industry for the production of antimicrobial drugs. It is also of interest in academic and research settings for the development of new antibiotic agents. Its application in the pharmaceutical industry is crucial for treating a wide range of bacterial infections. In terms of specific applications, it is used in the formulation of various antibiotic products. For more information on its use, consult the latest pharmaceutical industry reports or academic literature.

What precautions should be taken when handling Protected meropenem (CAS: 96036-02-1)?

When handling Protected meropenem, it is essential to wear appropriate personal protective equipment (PPE) including gloves and safety glasses. Work should be conducted in a well-ventilated area or a fume hood to minimize inhalation risks. Spills should be cleaned up immediately using appropriate absorbent materials. In case of accidental contact with skin or eyes, rinse with copious amounts of water and seek medical attention. Always refer to the safety data sheet (SDS) for detailed handling and emergency procedures.