Lithium Hydroxide → HCID 23114798, compound

HRID 748835Notes

Reaction equation

HRID 748835 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 and the mixture was stirred for 2 hours. After the addition of 10% sodium bisulfate, the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue thus obtained was crystallized from ethanol to yield the title compound (67 mg, 75%) as needle crystals.

Workup

  1. extractionthe 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. customThe residue thus obtained
  6. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-9ce69becdde749978d110d9e1bbe24bf
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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