Lithium hydroxide, monohydrate → HCID 68568078, compound

HRID 747635Notes

Reaction equation

HRID 747635 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)(=[O:17])=[O:16])[C@H:9]([C:11]([O:13]C)=[O:12])[CH3:10])=[C:4]([CH2:28][C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])[CH:3]=1.O.[OH-].[Li+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)(=[O:16])=[O:17])[C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[C:4]([CH2:28][C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])[CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68566108HCID 68566108, compound

Product 1

HCID 68568078HCID 68568078, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.373 g of methyl N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-N-[(3,4-dimethoxyphenyl)sulfonyl]alaninate dissolved in 20 ml of ethanol is added 0.52 g of lithium hydroxide monohydrate, and the mixture is left at room temperature for 18 hours. The medium is concentrated and the residue is taken up in ethyl acetate and washed with 5% potassium hydrogen sulfate solution. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a 90/10 (v/v) dichloromethane/methanol mixture to give 0.494 g of the expected product.

Workup

  1. concentrationThe medium is concentrated
  2. washwashed with 5% potassium hydrogen sulfate solution
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with a 90/10 (v/v) dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-47643d05152a47e18207c0d6c3cd1a56
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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