Product Name

  • Name

    RESATORVID

  • EINECS
  • CAS No. 243984-11-4
  • Article Data6
  • CAS DataBase
  • Density 1.39 g/cm3
  • Solubility
  • Melting Point 68-69 °C
  • Formula C15H17ClFNO4S
  • Boiling Point 461.958 °C at 760 mmHg
  • Molecular Weight 361.822
  • Flash Point 233.184 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 243984-11-4 (RESATORVID)
  • Hazard Symbols
  • Synonyms Resatorvid;(6R)-6-[[(2-Chloro-4-fluorophenyl)amino]sulfonyl]-1-cyclohexene-1-carboxylic acid ethyl ester;
  • PSA 80.85000
  • LogP 4.41660

Synthetic route

(6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid
890155-18-7

(6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid

ethanol
64-17-5

ethanol

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With sulfuric acid for 19h; Heating;72%
ethyl (6R)-6-{[[(2S)-2-(acetyloxy)-2-phenylacetyl]-(2-chloro-4-fluorophenyl)amino]sulfonyl}cyclohex-1-ene-1-carboxylate
415679-88-8

ethyl (6R)-6-{[[(2S)-2-(acetyloxy)-2-phenylacetyl]-(2-chloro-4-fluorophenyl)amino]sulfonyl}cyclohex-1-ene-1-carboxylate

A

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

B

acetic acid (2-chloro-4-fluoro-phenylcarbamoyl)-phenyl-methyl ester

acetic acid (2-chloro-4-fluoro-phenylcarbamoyl)-phenyl-methyl ester

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 0℃; for 2h;A 68%
B n/a
acetoxymethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
890155-23-4

acetoxymethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

ethanol
64-17-5

ethanol

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With sulfuric acid for 25h; Heating;65%
(1'S)-1'phenylethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
890155-19-8

(1'S)-1'phenylethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

ethanol
64-17-5

ethanol

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With sulfuric acid for 26h; Heating;37%
ethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
243983-70-2

ethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

A

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

B

ethyl (6S)-6-[N-(2-chloro-4-fluoro-phenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

ethyl (6S)-6-[N-(2-chloro-4-fluoro-phenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
HPLC-CHIRALPAK AD;A 634 mg
B 681 mg
ethyl (6R)-6-({(2-chloro-4-fluoro-phenyl)-[(2R)-4-methoxy-2-methyl-4-oxobutanoyl]amino}sulfonyl)cyclohex-1-ene-1-carboxylate

ethyl (6R)-6-({(2-chloro-4-fluoro-phenyl)-[(2R)-4-methoxy-2-methyl-4-oxobutanoyl]amino}sulfonyl)cyclohex-1-ene-1-carboxylate

A

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

B

ethyl (6S)-6-[N-(2-chloro-4-fluoro-phenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

ethyl (6S)-6-[N-(2-chloro-4-fluoro-phenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 0℃; for 2h; Title compound not separated from byproducts.;
ethyl 2-(chlorosulfonyl)cyclohex-1-ene-1-carboxylate
243984-26-1

ethyl 2-(chlorosulfonyl)cyclohex-1-ene-1-carboxylate

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / Et3N / ethyl acetate
2: 634 mg / HPLC-CHIRALPAK AD
View Scheme
2-(ethoxycarbonyl)cyclohex-1-ene-1-sulfonic acid
243984-25-0

2-(ethoxycarbonyl)cyclohex-1-ene-1-sulfonic acid

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2 / 14 h / Heating
2: 78 percent / Et3N / ethyl acetate
3: 634 mg / HPLC-CHIRALPAK AD
View Scheme
(6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid
340722-43-2

(6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 72 percent / Cs2CO3; tetrabutylammonium iodide / acetonitrile / 2.5 h / 52 - 55 °C
2: Lipase PS-D / acetone; H2O / 17.5 h / 28 °C
3: 72 percent / H2SO4 / 19 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 72 percent / Cs2CO3; tetrabutylammonium iodide / acetonitrile / 2.5 h / 52 - 55 °C
2: 48 percent / Lipase PS-D / acetone; H2O / 17.5 h / 28 °C
3: 65 percent / H2SO4 / 25 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 32 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 7 h
2: 84 percent / H2; AcOH / Pd/C / 2 h / atmospheric pressure
3: 72 percent / H2SO4 / 19 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 32 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 6 h
2: 37 percent / H2SO4 / 26 h / Heating
View Scheme
ethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
243983-70-2

ethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 74 percent / Ba(OH)2*8H2O / acetonitrile / 1 h / 60 °C
2: 72 percent / Cs2CO3; tetrabutylammonium iodide / acetonitrile / 2.5 h / 52 - 55 °C
3: Lipase PS-D / acetone; H2O / 17.5 h / 28 °C
4: 72 percent / H2SO4 / 19 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 74 percent / Ba(OH)2*8H2O / acetonitrile / 1 h / 60 °C
2: 72 percent / Cs2CO3; tetrabutylammonium iodide / acetonitrile / 2.5 h / 52 - 55 °C
3: 48 percent / Lipase PS-D / acetone; H2O / 17.5 h / 28 °C
4: 65 percent / H2SO4 / 25 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 74 percent / Ba(OH)2*8H2O / acetonitrile / 1 h / 60 °C
2: 32 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 7 h
3: 84 percent / H2; AcOH / Pd/C / 2 h / atmospheric pressure
4: 72 percent / H2SO4 / 19 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 74 percent / Ba(OH)2*8H2O / acetonitrile / 1 h / 60 °C
2: 32 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 6 h
3: 37 percent / H2SO4 / 26 h / Heating
View Scheme
acetoxymethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
340722-42-1

acetoxymethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Lipase PS-D / acetone; H2O / 17.5 h / 28 °C
2: 72 percent / H2SO4 / 19 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 48 percent / Lipase PS-D / acetone; H2O / 17.5 h / 28 °C
2: 65 percent / H2SO4 / 25 h / Heating
View Scheme
(1'R)-1'-(4-nitrophenyl)ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate
890155-20-1

(1'R)-1'-(4-nitrophenyl)ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / H2; AcOH / Pd/C / 2 h / atmospheric pressure
2: 72 percent / H2SO4 / 19 h / Heating
View Scheme
ethyl 2-mercaptocyclohex-1-ene-1-carboxylate
54928-91-5

ethyl 2-mercaptocyclohex-1-ene-1-carboxylate

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 74 percent / Cl2(gas); aq. AcOH / 0.83 h / 15 °C
2: 78 percent / Et3N / ethyl acetate
3: 634 mg / HPLC-CHIRALPAK AD
View Scheme
Multi-step reaction with 4 steps
1: sodium trioxoboran tetrahydrate; AcOH / 12 h / 50 - 85 °C
2: SOCl2 / 14 h / Heating
3: 78 percent / Et3N / ethyl acetate
4: 634 mg / HPLC-CHIRALPAK AD
View Scheme
ethyl 2-oxocyclohexane carboxylate
1655-07-8

ethyl 2-oxocyclohexane carboxylate

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: H2S(gas) / ethanol / 2 h / -50 °C
1.2: HCl(gas) / ethanol / 2 h / -20 °C
1.3: 73 percent / H2S(gas) / ethanol / 16 h / -20 °C
2.1: 74 percent / Cl2(gas); aq. AcOH / 0.83 h / 15 °C
3.1: 78 percent / Et3N / ethyl acetate
4.1: 634 mg / HPLC-CHIRALPAK AD
View Scheme
Multi-step reaction with 5 steps
1.1: H2S(gas) / ethanol / 2 h / -50 °C
1.2: HCl(gas) / ethanol / 2 h / -20 °C
1.3: 73 percent / H2S(gas) / ethanol / 16 h / -20 °C
2.1: sodium trioxoboran tetrahydrate; AcOH / 12 h / 50 - 85 °C
3.1: SOCl2 / 14 h / Heating
4.1: 78 percent / Et3N / ethyl acetate
5.1: 634 mg / HPLC-CHIRALPAK AD
View Scheme
ethyl 2-(chlorosulfonyl)cyclohex-1-ene-1-carboxylate
243984-26-1

ethyl 2-(chlorosulfonyl)cyclohex-1-ene-1-carboxylate

2-chloro-4-fluoroaniline
2106-02-7

2-chloro-4-fluoroaniline

A

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

B

ethyl (6S)-6-[N-(2-chloro-4-fluoro-phenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

ethyl (6S)-6-[N-(2-chloro-4-fluoro-phenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0℃; for 14.5h;
...Expand
C29H34ClFN4O8S2

C29H34ClFN4O8S2

A

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

B

C20H22ClFN4O4S

C20H22ClFN4O4S

Conditions
ConditionsYield
With water at 37℃; pH=7.4;
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

1-(phenylsulfonyl)-7-azido-2-heptanol
1346434-25-0

1-(phenylsulfonyl)-7-azido-2-heptanol

C29H34ClFN4O8S2

C29H34ClFN4O8S2

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; 1-(phenylsulfonyl)-7-azido-2-heptanol With pyridine In tetrahydrofuran
Stage #2: ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate With triethylamine In tetrahydrofuran		26%
...Expand
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

1-(phenylsulfonyl)-7-azido-2-heptyl chloroformate
1346434-36-3

1-(phenylsulfonyl)-7-azido-2-heptyl chloroformate

ethyl 6-((N-((7-azido-1-(phenylsulfonyl)heptan-2-yl)oxy)carbonyl)-N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate

ethyl 6-((N-((7-azido-1-(phenylsulfonyl)heptan-2-yl)oxy)carbonyl)-N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 2h;26%
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

1-(phenylsulfonyl)-7-azido-2-heptyl chloroformate
1346434-36-3

1-(phenylsulfonyl)-7-azido-2-heptyl chloroformate

C29H34ClFN4O8S2

C29H34ClFN4O8S2

Conditions
ConditionsYield
With trimethylamine In tetrahydrofuran at 20℃; for 2h;
ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate
243984-11-4

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate

C7H12ClN3O2
1346453-80-2

C7H12ClN3O2

A

(S)-ethyl 6-(N-(((6-azidohexyl)oxy)carbonyl)-N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate

(S)-ethyl 6-(N-(((6-azidohexyl)oxy)carbonyl)-N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate

B

(R)-ethyl 6-(N-(((6-azidohexyl)oxy)carbonyl)-N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate

(R)-ethyl 6-(N-(((6-azidohexyl)oxy)carbonyl)-N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane for 3h; Reagent/catalyst;
...Expand

Resatorvid Specification

The Resatorvid, with the CAS registry number 243984-11-4, is also known as UNII-H2MZ648C31. This chemical's molecular formula is C15H17ClFNO4S. Its IUPAC name is called ethyl (6R)-6-[(2-chloro-4-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate.

Physical properties of Resatorvid: (1)ACD/LogP: 3.02; (2)#H bond acceptors: 5; (3)#H bond donors: 1; (4)#Freely Rotating Bonds: 5; (5)Index of Refraction: 1.574; (6)Molar Refractivity: 85.313 cm3; (7)Molar Volume: 258.623 cm3; (8)Surface Tension: 52.008 dyne/cm; (9)Density: 1.399 g/cm3; (10)Flash Point: 233.184 °C; (11)Enthalpy of Vaporization: 72.292 kJ/mol; (12)Boiling Point: 461.958 °C at 760 mmHg; (13)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCOC(=O)C1=CCCCC1S(=O)(=O)NC2=C(C=C(C=C2)F)Cl
(2)Isomeric SMILES: CCOC(=O)C1=CCCC[C@H]1S(=O)(=O)NC2=C(C=C(C=C2)F)Cl
(3)InChI: InChI=1S/C15H17ClFNO4S/c1-2-22-15(19)11-5-3-4-6-14(11)23(20,21)18-13-8-7-10(17)9-12(13)16/h5,7-9,14,18H,2-4,6H2,1H3/t14-/m1/s1
(4)InChIKey: LEEIJTHMHDMWLJ-CQSZACIVSA-N

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