Lithium Hydroxide → (2-{[4-Chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-acetic acid

HRID 1848578Notes

Reaction equation

HRID 1848578 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]([C:14](=[O:30])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]2[CH:23]=[N:24][C:25]([Cl:29])=[CH:26][C:27]=2[CH3:28])[CH:16]=1)[CH3:13].[Li+].[OH-]>C1COCC1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]([N:12]([CH3:13])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][C:3]([OH:31])=[O:2])=[O:30])=[CH:16][C:17]=1[C:22]1[CH:23]=[N:24][C:25]([Cl:29])=[CH:26][C:27]=1[CH3:28]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59370345(2-{[4-Chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-acetic acid methyl ester

Product 1

HCID 59370372(2-{[4-Chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-{[4-Chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-acetic acid methyl ester (10 mg, 0.02 mmol) was dissolved in THF (300 μL) and 1M LiOH (100 μL) was added. The mixture was stirred at room temperature until LCMS indicated that starting material was completely consumed. The mixture was diluted with EtOAc and acidified with 1N HCl. The organic layer was concentrated, dissolved in MeOH and purified by prep LCMS to yield (2-{[4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-acetic acid 4-1. MS [M+H]+: 445.0; tR=6.75 min, (method 2)

Workup

  1. customwas completely consumed
  2. additionThe mixture was diluted with EtOAc
  3. concentrationThe organic layer was concentrated
  4. dissolutiondissolved in MeOH
  5. custompurified by prep LCMS

Sources & evidence

ORD record
ord-1b599cf36f0a407faba564266940f83c
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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