Lithium Hydroxide → HCID 59370334, compound

HRID 661636Notes

Reaction equation

HRID 661636 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([C:15](=[O:31])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([C:23]2[CH:24]=[N:25][C:26]([Cl:30])=[CH:27][C:28]=2[CH3:29])[CH:17]=1)[CH3:14].[Li+].[OH-]>C1COCC1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([N:13]([CH3:14])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][C:3]([OH:32])=[O:2])=[O:31])=[CH:17][C:18]=1[C:23]1[CH:24]=[N:25][C:26]([Cl:30])=[CH:27][C:28]=1[CH3:29]

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 59370348HCID 59370348, compound

Product 1

HCID 59370334HCID 59370334, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2-{[4-Chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenyl)-butyric acid methyl ester 13-1 (9 mg, 0.019 mmol) was dissolved in THF (0.2 mL) and 1M LiOH (0.15 mL) was added. After 1 hour extra 1N LiOH (0.15 mL) was added and the mixture was stirred at room temperature until LCMS indicated that starting material was completely consumed. The mixture was acidified with 1N HCl until pH ˜5, MeOH was added and purified by prep LCMS to yield 4-(2-{[4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenyl)-butyric acid 14-1. MS [M+H]+: 456.9; tR=7.33 min. (method 2)

Workup

  1. customwas completely consumed
  2. additionwas added
  3. custompurified by prep LCMS

Sources & evidence

ORD record
ord-c278e58f1c784708a7000e0c43b8e63f
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

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