HCID 59389328, compound → HCID 59389308, compound

HRID 2357925Notes

Reaction equation

HRID 2357925 reaction equation
C[Mg]Br.O1CCC[CH2:5]1.[C:9]([C:12]1[CH:30]=[C:15]2[C:16]([C:22]3[CH:23]([CH3:29])[CH2:24][C:25](=[O:28])[NH:26][N:27]=3)=[CH:17][CH:18]=[C:19]([O:20][CH3:21])[N:14]2[N:13]=1)(=[O:11])[CH3:10]>C1COCC1>[OH:11][C:9]([C:12]1[CH:30]=[C:15]2[C:16]([C:22]3[CH:23]([CH3:29])[CH2:24][C:25](=[O:28])[NH:26][N:27]=3)=[CH:17][CH:18]=[C:19]([O:20][CH3:21])[N:14]2[N:13]=1)([CH3:5])[CH3:10]

Participants

4

Reactant 2

HCID 59389328HCID 59389328, compoundHCID 178420675HCID 178420675, compound2×

Product 1

HCID 59389308HCID 59389308, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0.90 mol/L methyl magnesium bromide-tetrahydrofuran solution (0.614 mL) was added dropwise to a solution of the compound of Example 241 (55.4 mg) in THF (5 mL) at −78° C. in an argon atmosphere. The mixture was allowed to gradually warm to room temperature and was stirred for 3 hours. Subsequently, a second portion of 0.90 mol/L methyl magnesium bromide-tetrahydrofuran solution (0.614 mL) was added dropwise at −78° C. and the mixture was stirred at room temperature for another 3 hours. The reaction was then quenched by adding a saturated aqueous solution of ammonium chloride and the mixture was extracted with ethyl acetate (100 mL). The extract was washed with water and saturated brine and dried over anhydrous sodium sulfate. The dried extract was concentrated and purified by silica gel column chromatography (ethyl acetate) to afford the title compound as a pale yellow powder (14.0 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for another 3 hours
  2. customThe reaction was then quenched
  3. additionby adding a saturated aqueous solution of ammonium chloride
  4. extractionthe mixture was extracted with ethyl acetate (100 mL)
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. extractionThe dried extract
  8. concentrationwas concentrated
  9. custompurified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-32333a23298c41ebbff690c5cebaf459
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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