Hydrochloric Acid → HCID 21958032, compound

HRID 2299222Notes

Reaction equation

HRID 2299222 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11].Cl>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86758707HCID 86758707, compound2×

Product 1

HCID 21958032HCID 21958032, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of t-butyl [6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexen-1-yl]carbonyloxyacetate (Compound 59, 80 mg) obtained in Example 56 in ethyl acetate (4 ml), a 4N solution of hydrogen chloride in ethyl acetate (5 ml) was added with ice-cooling and the mixture was stirred at room temperature for 70 hours. The reaction mixture was evaporated under reduced pressure to dryness and the residue was purified by ODS column chromatography (eluent: methanol/water=3/2) to yield [6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexen-1-yl]carbonyloxyacetic acid (Compound 60, 25 mg) as white powdery crystals.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was evaporated under reduced pressure to dryness
  3. customthe residue was purified by ODS column chromatography (eluent: methanol/water=3/2)

Sources & evidence

ORD record
ord-27e50f150c9f4092a0574635a63dc291
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

Loading…