Water → HCID 57535895, compound

HRID 1455784Notes

Reaction equation

HRID 1455784 reaction equation
CON(C)[C:4](=[O:39])[CH:5]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:17]=2)=[CH:11][C:10]=1[Cl:30].[CH3:41][Mg+].[Br-].O>C1COCC1>[CH2:23]([O:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][CH:5]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:4](=[O:39])[CH3:41])=[C:10]([Cl:30])[CH:11]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23078159HCID 23078159, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 57535895HCID 57535895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound of Example 130-1 (570 mg) was dissolved in THF (15 mL). To this solution, a THF solution (2 mL) of 3 mol/L MeMgBr was added at 0° C. and the mixture was stirred for 3 hours. Following addition of water, the mixture was extracted with ethyl acetate and the extract was washed sequentially with water and a saturated aqueous solution of sodium chloride. The organic phase was then dried over anhydrous sodium sulfate. The solvent was removed and the residue was purified on a silica gel column chromatography (hexane:ethyl acetate=3:1) to give the desired product as a colorless oil (200 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed sequentially with water
  3. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified on a silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-c0111f55f5b5426c9cee31f19f87f481
Source dataset
uspto-grants-2009_01
Patent number
US07482491B2

Reaction notes

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