Lithium Hydroxide → HCID 18413994, compound

HRID 991454Notes

Reaction equation

HRID 991454 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:6]=1[S:15]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16].O1CCCC1.[OH-].[Li+]>CO.O>[CH3:14][O:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:5]([CH2:4][C:3]([OH:34])=[O:2])=[C:6]([S:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:26][N:25]=3)[CH2:20][CH2:19]2)(=[O:16])=[O:17])[CH:7]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 4446657Methyl 4,5-dimethoxy-2-[[4-[5-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl]sulfonyl]benzeneacetate

Product 1

HCID 18413994HCID 18413994, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

{4,5-Dimethoxy-2-[4-(5-trifluoromethylpyridin-2-yl)piperazine-1-sulfonyl]phenyl}acetic acid methyl ester (0.3 g) was taken up in methanol (10 ml), tetrahydrofuran (10 ml) and water (10 ml). Lithium hydroxide (125 mg) was added and the reaction stirred at RT for 16 hrs. The reaction was diluted with water (10 ml), its volume reduced to one third in vacuo, and the reaction extracted with diethyl ether (3×15 ml). The aqueous layer was acidified to pH 4 with 2M hydrochloric acid and extracted with ethyl acetate (4×25 ml). The combined ethyl acetate extracts were washed with water (25 ml) and brine (25 ml) and dried over sodium sulphate. The solvent was removed in vacuo to yield the title compound as a white solid (291 mg, 100%).

Workup

  1. extractionthe reaction extracted with diethyl ether (3×15 ml)
  2. extractionextracted with ethyl acetate (4×25 ml)
  3. washThe combined ethyl acetate extracts were washed with water (25 ml) and brine (25 ml)
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-438cf89834a5433d984fd49c1ae7848d
Source dataset
uspto-grants-2002_10
Patent number
US06465468B1

Reaction notes

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