Water → (2S)-3-(4-{2-[(2,4-Difluorobenzyl)(heptyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic Acid

HRID 854159Notes

Reaction equation

HRID 854159 reaction equation
[F:1][C:2]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:3]=1[CH2:4][N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[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.O.[OH-].[Li+]>C1COCC1>[F:1][C:2]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:3]=1[CH2:4][N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[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

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68857223Ethyl(2S)-3-(4-{2-[(2,4-difluorobenzyl)(heptyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate

Product 1

HCID 68856787(2S)-3-(4-{2-[(2,4-Difluorobenzyl)(heptyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoic AcidYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(2S)-3-(4-{2-[(2,4-difluorobenzyl)(heptyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate (0.047 g, 0.090 mmol) in THF (2.0 mL) was added water (2.0 mL) and lithium hydroxide (0.010 mg, 0.42 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, acidified with 2M HCl, and extracted with ethyl acetate (4×25 mL). The combined organic phase was washed with brine (25 m]L), dried over Na2SO4, and concentrated in vacuo to afford 0.044 g (89%) of a colourless oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate (4×25 mL)
  3. washThe combined organic phase was washed with brine (25 m]L),
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81f724ee4f514774b27aaf34bac88314
Source dataset
uspto-grants-2007_08
Patent number
US07256307B2

Reaction notes

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