Lithium Hydroxide → HCID 11466514, compound

HRID 1725231Notes

Reaction equation

HRID 1725231 reaction equation
[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[CH2:4][N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([O:22][CH2:23][CH3:24])[C:17]([O:19]CC)=[O:18])=[CH:11][CH:10]=1.[Li+].[OH-]>C1COCC1>[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[CH2:4][N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([O:22][CH2:23][CH3:24])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68856606HCID 68856606, compound

Product 1

HCID 11466514HCID 11466514, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(2S)-3-(4-{2-[(2,4-difluorobenzyl)(nonyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate (0.038 g, 0.070 mmol) in THF (3 mL) was added aqueous 0.10 M LiOH (2 mL) and the reaction mixture was stirred at room temperature overnight. After acidification with 5% HCl, the mixture was extracted with ethyl acetate (3×25 mL) and the combined organic phase was washed with brine (25 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to afford 0.034 g (94%) of a colourless oil.

Workup

  1. extractionAfter acidification with 5% HCl, the mixture was extracted with ethyl acetate (3×25 mL)
  2. washthe combined organic phase was washed with brine (25 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afadef52b3e94c2d88638ecdf366327f
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

Loading…