Sodium Hydroxide → HCID 22644962, compound

HRID 2414616Notes

Reaction equation

HRID 2414616 reaction equation
C[O:2][C:3](=[O:34])[CH:4]([NH:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]#[C:32][CH3:33])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1.[OH-].[Na+]>C1COCC1.CO>[CH2:30]([O:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([NH:19][CH:4]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)=[CH:7][CH:6]=2)[C:3]([OH:34])=[O:2])(=[O:21])=[O:22])=[CH:24][CH:25]=1)[C:31]#[C:32][CH3:33]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86587126HCID 86587126, compound

Product 1

HCID 22644962HCID 22644962, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl({[4-(2-butynyloxy)phenyl]sulfonyl}amino){4-[2-(1-pyrrolidinyl)ethoxy]phenyl}acetate (2.52 g, 5.19 mmol) and 5N NaOH (5.18 mL) in THF (32 mL) and methanol (32 mL) was stirred at room temperature for 2 h. After removing the solvent, the residue was dissolved in water and neutralized with HCl to pH˜6. The precipitated solid was filtered to provide 1.61 g of ({[4-(2-butynyloxy)phenyl]sulfonyl}amino){4-[2-(1-pyrrolidinyl)ethoxy]phenyl}acetic acid as a white solid. Yield 66%. mp 245-247° C. Electrospray Mass Spec 473.2 (M+H)+.

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in water and neutralized with HCl to pH˜6
  3. filtrationThe precipitated solid was filtered

Sources & evidence

ORD record
ord-95223fb865e542d7bbd46cb90188165d
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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