Lithium Hydroxide → HCID 59610025, compound

HRID 1889172Notes

Reaction equation

HRID 1889172 reaction equation
C([O:3][C:4](=[O:30])[CH:5]([O:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[F:29])[C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)C.[OH-].[Li+]>C1COCC1.CO.O>[F:29][C:23]1[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:22]=1[O:21][CH:5]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:4]([OH:30])=[O:3]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 59610054(2,4-Difluoro-phenoxy)-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid ethyl ester

Product 1

HCID 59610025HCID 59610025, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

(2,4-Difluoro-phenoxy)-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid ethyl ester (1.3 gm, 2.98 mmol) was dissolved in THF (5 ml) and methanol (0.5 ml). To this was added a solution of lithium hydroxide (0.62 gm, 14.90 mmol) in water (5 ml) and stirred for 18 hours at 25° C. Organic solvents were evaporated from the reaction mixture and aqueous layer was acidified with 1N HCl, precipitated product was filtered off and residue was washed with water. Solid product was dried under vacuum to provide (2,4-difluoro-phenoxy)-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid (1 gm).

Workup

  1. customOrganic solvents were evaporated from the reaction mixture and aqueous layer
  2. customprecipitated product
  3. filtrationwas filtered off
  4. washresidue was washed with water
  5. customSolid product was dried under vacuum

Sources & evidence

ORD record
ord-d1027e0fea88401288c8755ce296a37a
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

Loading…