Lithium hydroxide, monohydrate → HCID 68568258, compound

HRID 747640Notes

Reaction equation

HRID 747640 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:6]=1[N:13]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1)(=[O:22])=[O:21])[C@@H:14]([C:16]([O:18]C)=[O:17])[CH3:15].O.[OH-].[Li+]>O1CCOCC1.O>[F:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:6]=1[N:13]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1)(=[O:22])=[O:21])[C@@H:14]([C:16]([OH:18])=[O:17])[CH3:15]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58941206HCID 58941206, compound

Product 1

HCID 68568258HCID 68568258, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To 0.164 g of methyl N-[2-(2,6-difluorobenzyl)-6-methoxyphenyl]-N-[(3,4-dimethoxyphenyl)sulfonyl]-(R)-alaninate dissolved in 8 ml of a 1,4-dioxane/water mixture (4/1) is added, at room temperature, 0.015 g of lithium hydroxide monohydrate. The mixture is left at room temperature for 48 hours. The reaction medium is washed with 1M hydrochloric acid solution and extracted with ethyl acetate. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a dichloromethane/ethanol mixture to give 0.08 g of the expected product.

Workup

  1. additionis added, at room temperature
  2. washThe reaction medium is washed with 1M hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on a column of silica gel
  7. washeluting with a dichloromethane/ethanol mixture

Sources & evidence

ORD record
ord-92f71b14693d495f92aeb41ff618a70b
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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