Hydrochloric Acid → HCID 21958070, compound

HRID 2299223Notes

Reaction equation

HRID 2299223 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:18])[NH:9][CH2:10][C:11]([O:13][C:14](C)(C)[CH3:15])=[O:12])[CH:5]=[CH:4][C:3]=1[NH:19][S:20]([CH:23]1[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH2:26][CH2:25][CH2:24]1)(=[O:22])=[O:21].Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:18])[NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:4][C:3]=1[NH:19][S:20]([CH:23]1[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH2:26][CH2:25][CH2:24]1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21958028HCID 21958028, compound

Product 1

HCID 21958070HCID 21958070, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

Ethyl 6-[N-[2-chloro-4-(N-t-butoxycarbonylmethylcarbamoyl)phenyl]sulfamoyl]-1-cyclohexene-1-carboxylate (23 mg) was dissolved in ethyl acetate (0.5 ml) and then admixed with a 4N solution of hydrogen chloride in ethyl acetate (1.8 ml) and the mixture was stirred at room temperature for 51 hours. The reaction mixture was diluted with ethyl acetate and then washed twice with saturated brine. The ethyl acetate layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=11:14) to yield ethyl 6-[N-[2-chloro-4-(N-ethoxycarbonylmethylcarbamoyl)phenyl]sulfamoyl]-1-cyclohexene-1-carboxylate (Compound 63; 18 mg) as a colorless oil.

Workup

  1. washwashed twice with saturated brine
  2. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=11:14)

Sources & evidence

ORD record
ord-4dabbb1904fb44de9cac58e264113670
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

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