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

HRID 2084914Notes

Reaction equation

HRID 2084914 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-b1a1b48b9a9440c7b014437f374071d4
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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