Methyl iodide → (R)-2-(1-Methoxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid methyl ester

HRID 1796155Notes

Reaction equation

HRID 1796155 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:26])[C@@H:6]([C@H:16]([OH:25])[C:17]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:18])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:27]I>CN(C)C=O.O>[CH3:3][O:4][C:5](=[O:26])[C@@H:6]([CH:16]([O:25][CH3:27])[C:17]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:18])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69434738(R)-2-((S)-1-Hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid methyl ester

Product 1

HCID 69619099(R)-2-(1-Methoxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 114 mg, 2.86 mmol) was added to a solution of (R)-2-((S)-1-Hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid methyl ester (800 mg, 2.38 mmol) in dry dimethylformamide followed by addition of methyl iodide (0.74 ml, 11.9 mmol) and the reaction mixture was stirred for two hours at rt. The reaction was diluted with water and extracted with Ethyl acetate. The organic extracts were washed with water and brine, dried over MgSO4 and concentrated under reduced pressure to give the title compound as a colorless oil solid (660 mg).

Workup

  1. extractionextracted with Ethyl acetate
  2. washThe organic extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9acd84f93df047a99ab42877451fe89b
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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