Water → (2S)-3-(4-{2-[(Cyclohexylmethyl)(heptyl)amino]-2-oxoethoxy}phenyl)-2-ethoxy-propanoic acid

HRID 1725209Notes

Reaction equation

HRID 1725209 reaction equation
[CH:1]1([CH2:7][N:8]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:9](=[O:28])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:25][CH2:26][CH3:27])[C:20]([O:22]CC)=[O:21])=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+]>C1COCC1>[CH:1]1([CH2:7][N:8]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:9](=[O:28])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:25][CH2:26][CH3:27])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 11465983Ethyl(2S)-3-(4-{2-[(cyclohexylmethyl)(heptyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate

Product 1

HCID 9955970(2S)-3-(4-{2-[(Cyclohexylmethyl)(heptyl)amino]-2-oxoethoxy}phenyl)-2-ethoxy-propanoic acidYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(2S)-3-(4-{2-[(cyclohexylmethyl)(heptyl)amino]-2-oxoethoxy}phenyl)-2-ethoxy-propanoate (0.031 g, 0.057 mmol) in THF (2.0 mL) were added water (2.0 mL) and lithium hydroxide (0.006 g, 0.26 mmol), and the reaction mixture was stirred at room temperature overnight. The mixture was acidified with 2M HCI and extracted with ethyl acetate (4×25 mL). The combined organic phase was washed with brine (25 mL), dried over Na2SO4, and concentrated in vacuo to afford 0.027 g (93%) of a colourless oil.

Workup

  1. extractionextracted with ethyl acetate (4×25 mL)
  2. washThe combined organic phase was washed with brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64444598bae642d0be4115265afe4646
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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