Lithium Hydroxide → HCID 59370334, compound

HRID 448883Notes

Reaction equation

HRID 448883 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-b52ad8b07bd342f280d9a3ba44a6f6f8
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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