Hydrochloric Acid → N-[4-(1,3-benzodioxol-5-yl)-1-benzyl-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide

HRID 1368620Notes

Reaction equation

HRID 1368620 reaction equation
[Na].C([O:5][CH2:6][CH2:7][O:8][C:9]1[C:13]([C:14]2[CH:22]=[CH:21][C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=2)=[C:12]([N:23](S(C2C=CC(C(C)(C)C)=CC=2)(=O)=O)[S:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[N:11]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[N:10]=1)(=O)C.Cl>C(O)C.O>[O:18]1[C:17]2[CH:21]=[CH:22][C:14]([C:13]3[C:9]([O:8][CH2:7][CH2:6][OH:5])=[N:10][N:11]([CH2:50][C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[C:12]=3[NH:23][S:24]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([CH3:36])([CH3:34])[CH3:35])=[CH:31][CH:32]=3)(=[O:26])=[O:25])=[CH:15][C:16]=2[O:20][CH2:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 222819612-{[4-(1,3-benzodioxol-5-yl)-1-benzyl-5-(bis{[4-(tert-butyl)phenyl]sulfonyl)amino)-1H-pyrazol-3-yl]oxy}ethyl acetate

Product 1

HCID 22281905N-[4-(1,3-benzodioxol-5-yl)-1-benzyl-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamideYield 95.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

An aqueous solution of sodium hydroxyde (2N, 75 ml) was added at room temperature to a solution of 2-{[4-(1,3-benzodioxol-5-yl)-1-benzyl-5-(bis{[4-(tert-butyl)phenyl]sulfonyl}amino)-1H-pyrazol-3-yl]oxy}ethyl acetate (Preparation 52) (24 g) in ethanol (300 ml) and left overnight. The reaction mixture was then diluted with water (1000 ml), acidified with an aqueous solution of HCl (1N) and extracted with ethyl acetate (3×500 ml). The combined organic phases were washed with brine (500 ml) and concentrated under reduced pressure. The yellow oil was purified by column chromatography (silica, 500 g) eluted with hexane:ethyl acetate (1:1) yielding the title compound as a pale beige solid (16 g).

Workup

  1. extractionextracted with ethyl acetate (3×500 ml)
  2. washThe combined organic phases were washed with brine (500 ml)
  3. concentrationconcentrated under reduced pressure
  4. customThe yellow oil was purified by column chromatography (silica, 500 g)
  5. washeluted with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-78c969e5c5cd4b778d5c7eec227f6e15
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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