Lithium Hydroxide → HCID 11249399, compound

HRID 1725249Notes

Reaction equation

HRID 1725249 reaction equation
[CH2:1]([O:8][C:9]1[CH:40]=[CH:39][C:12]([CH2:13][N:14]([CH2:35][CH2:36][CH2:37][CH3:38])[C:15](=[O:34])[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([O:31][CH2:32][CH3:33])[C:26]([O:28]CC)=[O:27])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C(#N)C.O.[OH-].[K+]>[CH2:1]([O:8][C:9]1[CH:40]=[CH:39][C:12]([CH2:13][N:14]([CH2:35][CH2:36][CH2:37][CH3:38])[C:15](=[O:34])[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([O:31][CH2:32][CH3:33])[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 68855201HCID 68855201, compound

Product 1

HCID 11249399HCID 11249399, compoundYield 64.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 14797Potassium HydroxideSolvent

Procedure

To a solution of ethyl(2S)-3-(4-{2-[[4-(benzyloxy)benzyl](butyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate (0.116 g, 0.21 mmol) in acetonitrile (10 mL) was added aqueous 0.10 M LiOH (5 mL) and the reaction mixture was stirred at room temperature overnight. The solvent volume was reduced in vacuo and the remaining aqueous phase was diluted with water and aqueous 1 M KOH and washed with diethyl ether (2×50 mL). The aqueous phase was acidified with 5% HCl and extracted with ethyl acetate (3×50 mL). The combined organic phase was washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo to afford 0.070 g (63%) of a colourless oil.

Workup

  1. washwashed with diethyl ether (2×50 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic phase was washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb68e542b38d49c4b9e4577966494e54
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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