Lithium Hydroxide → HCID 23114798, compound

HRID 2080393Notes

Reaction equation

HRID 2080393 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22]C)=[O:21])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Li+].S([O-])(O)(=O)=O.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 23114666HCID 23114666, compound

Product 1

HCID 23114798HCID 23114798, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (5 ml) was dissolved methyl 3-[6-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridin-3-yl]propionate (92 mg, 0.20 mmol). An aqueous solution (3 ml) of lithium hydroxide (23 mg, 0.5 mmol) was added to the resulting solution and the mixture was stirred for 2 hours. After addition of 10% sodium hydrogensulfate, the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue. The resulting residue was crystallized from ethanol to give the title compound (67 mg, 75%) as needle crystals.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue
  6. customThe resulting residue was crystallized from ethanol

Sources & evidence

ORD record
ord-ae7a1e6960314cbc8fe13ae028af234f
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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