Methyl iodide → HCID 69639709, compound

HRID 1245399Notes

Reaction equation

HRID 1245399 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6](=[O:37])[CH2:7][CH:8]([S:33][C:34](=O)C)[CH:9]1[O:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:24]([CH3:32])[CH:23]=3)=[CH:16][CH:15]=2)[CH2:10]1.CI>CO>[CH3:4][O:5][C:6](=[O:37])[CH2:7][CH:8]([CH:9]1[O:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:24]([CH3:32])[CH:23]=3)=[CH:16][CH:15]=2)[CH2:10]1)[S:33][CH3:34]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 86592945HCID 86592945, compound

Product 1

HCID 69639709HCID 69639709, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (28% in methanol) (0.050 mL, 0.22 mmol) was added to a suspension of the product from step 11b (0.085 g, 0.18 mmol) in methanol (1.5 mL) at room temperature. The reaction turned clear and was stirred for 45 minutes, and then methyl iodide (0.05 mL, 0.80 mmol) was added. The reaction was stirred an additional 45 minutes, quenched with aqueous ammonium chloride, concentrated to remove the methanol, and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried with magnesium sulfate, and concentrated to give 3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-3-methylsulfanyl-propionic acid methyl ester (0.08 g, 99%) as an oil. MS found: (M+H)+=451.

Workup

  1. stirringThe reaction was stirred an additional 45 minutes
  2. customquenched with aqueous ammonium chloride
  3. concentrationconcentrated
  4. customto remove the methanol
  5. custompartitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-77a148c2fc744cbdacaec90343643539
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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