Methyl iodide → HCID 58979302, compound

HRID 1181120Notes

Reaction equation

HRID 1181120 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][OH:31])([CH3:4])([CH3:3])[CH3:2].[CH3:33]I.[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][O:31][CH3:33])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58979414HCID 58979414, compound

Product 1

HCID 58979302HCID 58979302, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 15 mL round bottomed flask was charged with 3-{2-hydroxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid tert-butyl ester (0.10 g, 0.23 mmol) and methyl iodide (0.21 mL, 2.3 mmol) in anhydrous DMF (1 mL) under a nitrogen atmosphere. The mixture was cooled in an ice bath and treated in one portion with NaH (0.018 g, 0.25 mmol, 60% oil dispersion). The reaction mixture was stirred for 2 h, concentrated, and diluted with EtOAc (40 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated. The crude product was purified using radial chromatography (EtOAc:hexanes 10:90 to 25:75) to give a yellow oil (0.060 g, 58%). MS (ES) m/e 648 (M+1).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. concentrationconcentrated
  3. additiondiluted with EtOAc (40 mL)
  4. washThe organic layer was washed with brine (2×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-222e3f3683f14096a0f1ab54792015d9
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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