Hydrochloric Acid → HCID 22281989, compound

HRID 1368619Notes

Reaction equation

HRID 1368619 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][CH2:12][O:13][C:14]1[C:18]([C:19]2[CH:27]=[CH:26][C:22]3[O:23][CH2:24][O:25][C:21]=3[CH:20]=2)=[C:17]([N:28](S(C2C=CC(C(C)(C)C(OCC)=O)=CC=2)(=O)=O)[S:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([CH3:45])([CH3:44])[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[N:16]([CH3:63])[N:15]=1)(=O)C.[Cl-].[NH4+].Cl>CO.ClCCl>[O:23]1[C:22]2[CH:26]=[CH:27][C:19]([C:18]3[C:14]([O:13][CH2:12][CH2:11][OH:10])=[N:15][N:16]([CH3:63])[C:17]=3[NH:28][S:29]([C:32]3[CH:33]=[CH:34][C:35]([C:38]([CH3:45])([CH3:44])[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:36][CH:37]=3)(=[O:31])=[O:30])=[CH:20][C:21]=2[O:25][CH2:24]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 22281982HCID 22281982, compound

Product 1

HCID 22281989HCID 22281989, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Solid potassium carbonate (290 mg) was added at room temperature to a solution of impure ethyl 2-{4-[([3-[2-(acetyloxy)ethoxy]-4-(1,3-benzodioxol-5-yl)-1-methyl-1H-pyrazol-5-yl]{[4-(2-ethoxy-1,1-dimethyl-2-oxoethyl)phenyl]sulfonyl}amino)sulfonyl]phenyl}-2-methylpropanoate (Preparation 51) in a mixture of methanol (3 ml) and dichloromethane (3 ml). The reaction was left overnight, then an aqueous saturated solution of ammonium chloride (10 ml) was added. The aqueous phase was acidified by the addition of an aqueous solution of HCl (1N, few drops), the phases were separated and the aqueous phase was extracted with dichloromethane (2×10 ml). The organic fraction was dried over sodium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography (silica, 3.5 g) eluted with hexane:ethyl acetate (1:1) yielding the title compound as a colourless oil (240 mg).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane (2×10 ml)
  3. dry with materialThe organic fraction was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by column chromatography (silica, 3.5 g)
  6. washeluted with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-e8fa03d04a1446d99e739b5b09395562
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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