Ammonium Chloride → HCID 59389293, compound

HRID 2357912Notes

Reaction equation

HRID 2357912 reaction equation
[CH2:1]([C:3]1[CH:20]=[C:6]2[C:7]([C:13]3([CH2:18][CH3:19])[O:17][CH2:16][CH2:15][O:14]3)=[CH:8][CH:9]=[C:10]([CH:11]=[O:12])[N:5]2[N:4]=1)[CH3:2].[CH3:21][Mg]Br.C1COCC1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([C:3]1[CH:20]=[C:6]2[C:7]([C:13]3([CH2:18][CH3:19])[O:14][CH2:15][CH2:16][O:17]3)=[CH:8][CH:9]=[C:10]([CH:11]([OH:12])[CH3:21])[N:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59389319HCID 59389319, compoundHCID 178420675HCID 178420675, compound

Product 1

HCID 59389293HCID 59389293, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 152 (321 mg) was dissolved in THF (12.0 mL) in an argon atmosphere. While the solution was kept at −78° C., 0.90 mol/L methyl magnesium bromide/THF solution (1.70 mL) was added dropwise and the mixture was stirred for 3.5 hours as it was allowed to gradually warm to room temperature. Subsequently, a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent afforded the title compound as a yellow oil (340 mg).

Workup

  1. customwas kept at −78° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed sequentially with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8b2b14030f434b508ec66f31fdc6a711
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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