Lithium hydroxide, monohydrate → 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoic acid

HRID 20560Notes

Reaction equation

HRID 20560 reaction equation
[OH:1][CH2:2][C@H:3]([CH3:33])[O:4][C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:23]([NH:25][C:26]2[CH:31]=[N:30][C:29]([CH3:32])=[CH:28][N:27]=2)=[O:24])[CH:22]=1)[O:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][CH:10]=1.O.[OH-].[Li+]>C1COCC1.O>[OH:1][CH2:2][C@H:3]([CH3:33])[O:4][C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:23]([NH:25][C:26]2[CH:31]=[N:30][C:29]([CH3:32])=[CH:28][N:27]=2)=[O:24])[CH:22]=1)[O:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59346869ethyl 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoate

Product 1

HCID 593469134-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoic acidYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoate (0.4 g, 0.88 mmol) in THF (16 mL) was added to a solution of lithium hydroxide monohydrate (0.19 g, 4.43 mmol) in water (8 mL). The mixture was stirred at RT for 72 hours and the THF removed in vacuo. The aqueous layer was acidified with 1M hydrochloric acid (10 mL), and the solid precipitate filtered off, washed with water and dried in vacuo to give the desired compound (0.22 g). The material was used without further purification.

Workup

  1. customthe THF removed in vacuo
  2. filtrationthe solid precipitate filtered off
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1ac15f173aa548a09841427798985db5
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

Loading…