Sodium Hydroxide → HCID 22282012, compound

HRID 1368602Notes

Reaction equation

HRID 1368602 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[C:11]([N:20](S(C2C=CC(C(C)(C)C)=CC=2)(=O)=O)[S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[N:10]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[N:9]=1)(=O)C.[OH-].[Na+]>C(O)C>[CH2:47]([N:10]1[C:11]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:8]([O:7][CH2:6][CH2:5][OH:4])=[N:9]1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22281932HCID 22281932, compound

Product 1

HCID 22282012HCID 22282012, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of 2-{[1-benzyl-5-(bis{[4-(tert-butyl)phenyl]sulfonyl}amino)4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (Preparation 40) (1.01 g) in ethanol (20 ml) was slowly added sodium hydroxide solution (2M, 2 ml). The reaction mixture was left stirring at room temperature overnight. The solvent was removed in vacuo and the residue was taken up in ethyl acetate (30 ml) and washed with water (15 ml) followed by brine (15 ml). It was then dried (MgSO4) and the solvent removed in vacuo to yield the crude material as a yellow oil (ca.1 g). Purification was achieved using the Biotage™ Flash 40 system (silica, 90 g) with a gradient elution of hexane (75% to 65%) and ethyl acetate (25% to 35%) to yield the title product as a yellow solid (250 mg).

Workup

  1. waitThe reaction mixture was left
  2. customThe solvent was removed in vacuo
  3. washwashed with water (15 ml)
  4. dry with materialIt was then dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto yield the crude material as a yellow oil (ca.1 g)
  7. customPurification
  8. washwith a gradient elution of hexane (75% to 65%) and ethyl acetate (25% to 35%)

Sources & evidence

ORD record
ord-b5c09431ec28458780732d77d7d5273f
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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