Lithium Hydroxide → 2-[{[4-(2-Butynyloxy)phenyl]sulfonyl)(methyl)amino]-2-(4-chlorophenyl)acetic acid

HRID 1976450Notes

Reaction equation

HRID 1976450 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH3:28])[CH:16]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:17]([O:19]C)=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[OH-].[Li+]>>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]([CH3:28])[CH:16]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:17]([OH:19])=[O:18])(=[O:13])=[O:14])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 22645093Methyl 2-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-2-(4-chlorophenyl)acetate

Product 1

HCID 226448912-[{[4-(2-Butynyloxy)phenyl]sulfonyl)(methyl)amino]-2-(4-chlorophenyl)acetic acid

Procedure

This ester was reacted with excess methanolic lithium hydroxide at room temperature, followed by evaporation of the methanol. The residue was dissolved in water and acidified with 2N hydrochloric acid to give 2-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-2-(4-chlorophenyl)acetic acid as colorless crystals, mp 170-172° C., Electrospray Mass Spec 406.4 (M−H)−

Workup

  1. customfollowed by evaporation of the methanol
  2. dissolutionThe residue was dissolved in water

Sources & evidence

ORD record
ord-82ce77d398a643e3a1499223522d59f9
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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