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

HRID 2414620Notes

Reaction equation

HRID 2414620 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-f26bb8221fbc4bff876d6b8206256a21
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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