Sodium Hydroxide → HCID 22281907, compound

HRID 397277Notes

Reaction equation

HRID 397277 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:21]=[CH:20][C:16]3[O:17][CH2:18][O:19][C:15]=3[CH:14]=2)=[C:11]([N:22](S(C2C=CC(C(C)C)=CN=2)(=O)=O)[S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][N:27]=2)(=[O:25])=[O:24])[N:10]([CH3:47])[N:9]=1)(=O)C.[OH-].[Na+]>C(O)C>[O:17]1[C:16]2[CH:20]=[CH:21][C:13]([C:12]3[C:8]([O:7][CH2:6][CH2:5][OH:4])=[N:9][N:10]([CH3:47])[C:11]=3[NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][N:27]=3)(=[O:25])=[O:24])=[CH:14][C:15]=2[O:19][CH2:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 222819602-[(4-(1,3-benzodioxol-5-yl)-5-{bis[(5-isopropyl-2-pyridinyl)sulfonyl]amino}-1-methyl-1H-pyrazol-3-yl)oxy]ethyl acetate

Product 1

HCID 22281907HCID 22281907, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[(4-(1,3-benzodioxol-5-yl)-5{-bis[(5-isopropyl-2-pyridinyl)sulfonyl]amino}-1-methyl-1H-pyrazol-3-yl)oxy]ethyl acetate (Preparation 14) (9.0 g) in ethanol (200 ml) was added 2.0M aqueous sodium hydroxide (25 ml). The reaction was stirred for 30 min and concentrated under reduced pressure and the residue was poured onto 0.5M aqueous citric acid (300 ml). This was extracted with ethyl acetate (3×80 ml) and dried over magnesium sulfate. The solvent was removed under reduced pressure and the crude residue was purified by silica (230 g) chromatography eluting with a gradient of 50% ethyl acetate in hexane to 70% ethyl acetate in hexane to afford the title product as a white solid (5.0 g)

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionthe residue was poured onto 0.5M aqueous citric acid (300 ml)
  3. extractionThis was extracted with ethyl acetate (3×80 ml)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe crude residue was purified by silica (230 g) chromatography
  7. washeluting with a gradient of 50% ethyl acetate in hexane to 70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ee1111db13214b159a2adfc494df81c2
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

Loading…