Sulopenem

Base Information

• Chemical Name: Sulopenem
• CAS No.: 120788-07-0
• Molecular Formula: C12H15 N O5 S3
• Molecular Weight: 349.453
• UNII: XX514BJ1XW
• DSSTox Substance ID: DTXSID20869656
• Wikipedia: Sulopenem
• NCI Thesaurus Code: C84189
• Metabolomics Workbench ID: 155393
• ChEMBL ID: CHEMBL1908305
• Mol file: 120788-07-0.mol

Synonyms:CP 70429;CP-70,429;CP-70429;sulopenem

Chemical Property of Sulopenem

Chemical Property:

• Vapor Pressure: 3.2E-22mmHg at 25°C
• Boiling Point: 693.1°Cat760mmHg
• PKA: 3.88±0.40(Predicted)
• Flash Point: 373°C
• PSA: 164.72000
• Density: 1.74g/cm³
• LogP: 1.21000
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 349.01123610
• Heavy Atom Count: 21
• Complexity: 563

Purity/Quality:

99% ^*data from raw suppliers

Sulopenem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C2N(C1=O)C(=C(S2)SC3CCS(=O)C3)C(=O)O)O
• Isomeric SMILES: C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)S[C@H]3CC[S@@](=O)C3)C(=O)O)O
• Recent ClinicalTrials: Safety, Tolerability, and Pharmacokinetics of Sulopenem in Adolescents
• Recent EU Clinical Trials: A prospective, Phase 3, randomized, multi-center, double-blind, double dummy study of the efficacy, tolerability and safety of intravenous sulopenem followed by oral sulopenem-etzadroxil with probenecid versus intravenous ertapenem followed by oral ciprofloxacin or amoxicillin-clavulanate for treatment of complicated urinary tract infections in adults.
• Description: Sulopenem is a parenteral penem that demonstrates high activity against Gram-positive, Gram-negative, and anaerobic bacteria. Since it is stable in relation to renal dehydropeptidase I, it does not require concomitant administration of an inhibitor of this enzyme.
• Uses: Antibacterial. Sulopenem is a β-Lactamase inhibitor which is used in treatment of microbial infections. It is an important reagent for many drugs synthesized against bacterial infections.

Technology Process of Sulopenem

There total 11 articles about Sulopenem which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

(3S)-3-({(5R,6S)-6-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]-2-carboxy-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3 yl}sulfanyl)tetrahydrothiophenium-1-olate (770673-33-1) → (3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate (120788-07-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 18h; Inert atmosphere;

DOI:10.1021/op300131e

Reference yield:

3(S)-<thio>thiolane 1(R)-oxide sodium salt (120735-10-6,120735-20-8,126688-47-9) → (3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate (120788-07-0)

Guidance literature:

Multi-step reaction with 5 steps

1: propan-2-ol; CS₂ / 0.5 h / 3 °C

2: 98 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 0.25 h / -55 - -50 °C

3: 56 percent / P(OEt)3 / CHCl₃ / 10 h / Heating

4: 83 percent / glacial acetic acid, tetrabutylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature

5: 1.) triphenylphosphine, tetrakis(triphenylphosphine)palladium⁽⁰⁾, sodium 2-ethylhexamoate, 2.) 1 N HCl / 1.) rt, 2.) H₂O, 0 - 5 deg C, 45 min

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; triethyl phosphite; sodium 2-ethylhexanoic acid; In tetrahydrofuran; carbon disulfide; dichloromethane; chloroform; isopropyl alcohol;

DOI:10.1021/jo00042a010

Reference yield:

(3S,4R)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-<<<(1(R)-oxo-3(S)-thiolanyl)thio>thiocarbonyl>thio>-2-azetidinone (112206-93-6,112295-83-7,115793-24-3,142507-63-9) → (3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate (120788-07-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 0.25 h / -55 - -50 °C

2: 56 percent / P(OEt)3 / CHCl₃ / 10 h / Heating

3: 83 percent / glacial acetic acid, tetrabutylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature

4: 1.) triphenylphosphine, tetrakis(triphenylphosphine)palladium⁽⁰⁾, sodium 2-ethylhexamoate, 2.) 1 N HCl / 1.) rt, 2.) H₂O, 0 - 5 deg C, 45 min

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; triethyl phosphite; sodium 2-ethylhexanoic acid; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1021/jo00042a010

upstream raw materials:

2-Chloroallyl (5R,6S)-6-(1(R)-hydroxyethyl)-2-<(1(R)-oxo-3(S)-thiolanyl)thio>-2-penem-3-carboxylate

3(S)-<thio>thiolane 1(R)-oxide sodium salt

(3S,4R)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-<<<(1(R)-oxo-3(S)-thiolanyl)thio>thiocarbonyl>thio>-2-azetidinone

2-Chloroallyl (5R,6S)-6-<1(R)-<(dimethyl-tert-butylsilyl)oxy>ethyl>-2-<(1(R)-oxo-3(S)-thiolanyl)thio>-2-penem-3-carboxylate

Refernces

• 1、 -. "Process for removal of allyl group or allyloxycarbonyl group". . . Retrieved 2008/06/13.
• 2、 Volkmann, Robert A.,Kelbaugh, Paul R.,Nason, Deane M.,Jasys, V. John. "2-Thioalkyl Penems: An Efficient Synthesis of Sulopenem, a (5R,6S)-6-(1(R)-Hydroxyethyl)-2--2-penem Antibacterial". . p. 4352 - 4361. Retrieved 2007/10/02.