2-(2-Fluoroethylthio)-6-(1-hydroxyethyl)penem-3-carboxylate

Base Information

• Chemical Name: 2-(2-Fluoroethylthio)-6-(1-hydroxyethyl)penem-3-carboxylate
• CAS No.: 91685-69-7
• Molecular Formula: C₈H₉NO₄S
• Molecular Weight: 215.23
• DSSTox Substance ID: DTXSID60238665
• Wikidata: Q83120956
• Mol file: 91685-69-7.mol

Synonyms:2-(2-fluoroethylthio)-6-(1-hydroxyethyl)penem-3-carboxylate;2-FTHPC

Chemical Property of 2-(2-Fluoroethylthio)-6-(1-hydroxyethyl)penem-3-carboxylate

Chemical Property:

• Vapor Pressure: 1.02E-12mmHg at 25°C
• Boiling Point: 514°Cat760mmHg
• Flash Point: 264.7°C
• Density: 1.67g/cm³
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 215.02522894
• Heavy Atom Count: 14
• Complexity: 340

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1C2N(C1=O)C(=CS2)C(=O)O)O
• Isomeric SMILES: C[C@H]([C@H]1[C@@H]2N(C1=O)C(=CS2)C(=O)O)O

Technology Process of 2-(2-Fluoroethylthio)-6-(1-hydroxyethyl)penem-3-carboxylate

There total 22 articles about 2-(2-Fluoroethylthio)-6-(1-hydroxyethyl)penem-3-carboxylate 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:

2,2-dimethyl-trans-8-(α-hydroxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (73845-15-5,73890-34-3,91685-53-9,91685-54-0) → erythro-trans-6-(1-hydroxyethyl)penem-3-carboxylic acid (73845-25-7,73845-26-8,78560-93-7,78560-94-8,91685-69-7,91685-70-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 80 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 1) room temperature, 1 h; 2) reflux, 6 h

2: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1) -10 deg C, 30 min; 2) 0 deg C, 1 h

3: 36 percent / acetic acid, water / 1.75 h / Heating

4: 1.) aq. sodium hydroxide / 1) ethanol, -10 deg C, 5 min; 2) 2 deg C, 80 min

5: molecular sieves / dimethylformamide; toluene / 16 h / 30 °C

6: thionyl chloride, triethylamine / tetrahydrofuran / 0.5 h / 0 °C

7: 2.) aq. sodium carbonate / 1) THF, room temperature, 2 d

8: 1.) ozone, oxygen, trifluoroacetic acid, 2.) dimethyl sulfide, 3.) aq. KHCO₃ / 1) methylene chloride, -20 deg C (15 min); 2) 10 deg C, 10 min; 4) methylene chloride, reflux, 90 min

9: 80 percent / hydrogen / palladium on carbon / aq. ethanol; acetonitrile / 2.5 h / Ambient temperature

10: aq. sodium hydroxide / H₂O / 0.5 h / 0 °C

11: acidic cation exchange resin

With dmap; sodium hydroxide; thionyl chloride; molecular sieve; dimethylsulfide; acidic cation exchange resin; water; hydrogen; oxygen; sodium carbonate; potassium hydrogencarbonate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00526a045

Reference yield:

2,2-dimethyl-trans-8-(α-hydroxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (73845-15-5,73890-34-3,91685-53-9,91685-54-0) → threo-trans-6-(α-hydroxyethyl)penem-3-carboxylic acid (73845-25-7,73845-26-8,78560-93-7,78560-94-8,91685-69-7,91685-70-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 80 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 1) room temperature, 1 h; 2) reflux, 6 h

2: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1) -10 deg C, 30 min; 2) 0 deg C, 1 h

3: 19 percent / acetic acid, water / 1.75 h / Heating

4: 1.) aq. sodium hydroxide / 1) ethanol, -10 deg C, 5 min; 2) 2 deg C, 80 min

5: 100 percent / molecular sieves / dimethylformamide; toluene / 16 h / 30 °C

6: 100 percent / thionyl chloride, triethylamine / tetrahydrofuran / 0.5 h / 0 °C

7: 2.) aq. sodium carbonate / 1) THF, room temperature, 2 d

8: 1.) ozone, oxygen, trifluoroacetic acid, 2.) dimethyl sulfide, 3.) aq. KHCO₃ / 1) methylene chloride, -20 deg C (15 min); 2) 10 deg C, 10 min; 4) methylene chloride, reflux, 90 min

9: 80 percent / hydrogen / palladium on carbon / aq. ethanol; acetonitrile / 2.5 h / Ambient temperature

10: 60 percent / aq. sodium hydroxide / acetonitrile; H₂O / 0.5 h / 0 °C

11: acidic cation exchange resin / H₂O

With dmap; sodium hydroxide; thionyl chloride; molecular sieve; dimethylsulfide; acidic cation exchange resin; water; hydrogen; oxygen; sodium carbonate; potassium hydrogencarbonate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00526a045

Reference yield:

2,2-dimethyl-trans-8-(α-p-nitrobenzyloxycarbonyloxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (73845-16-6,73890-35-4,91685-55-1,91685-56-2) → erythro-trans-6-(1-hydroxyethyl)penem-3-carboxylic acid (73845-25-7,73845-26-8,78560-93-7,78560-94-8,91685-69-7,91685-70-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1) -10 deg C, 30 min; 2) 0 deg C, 1 h

2: 36 percent / acetic acid, water / 1.75 h / Heating

3: 1.) aq. sodium hydroxide / 1) ethanol, -10 deg C, 5 min; 2) 2 deg C, 80 min

4: molecular sieves / dimethylformamide; toluene / 16 h / 30 °C

5: thionyl chloride, triethylamine / tetrahydrofuran / 0.5 h / 0 °C

6: 2.) aq. sodium carbonate / 1) THF, room temperature, 2 d

7: 1.) ozone, oxygen, trifluoroacetic acid, 2.) dimethyl sulfide, 3.) aq. KHCO₃ / 1) methylene chloride, -20 deg C (15 min); 2) 10 deg C, 10 min; 4) methylene chloride, reflux, 90 min

8: 80 percent / hydrogen / palladium on carbon / aq. ethanol; acetonitrile / 2.5 h / Ambient temperature

9: aq. sodium hydroxide / H₂O / 0.5 h / 0 °C

10: acidic cation exchange resin

With sodium hydroxide; thionyl chloride; molecular sieve; dimethylsulfide; acidic cation exchange resin; water; hydrogen; oxygen; sodium carbonate; potassium hydrogencarbonate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00526a045

upstream raw materials:

Sodium; (5R,6S)-6-((S)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

2,2-dimethyl-trans-8-(α-hydroxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

2,2-dimethyl-trans-8-(α-p-nitrobenzyloxycarbonyloxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

2,2-dimethyl-trans-8-(α-p-nitrobenzyloxycarbonyloxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane 6-dioxide

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