Hydrochloric Acid → HCID 11439168, compound

HRID 1350088Notes

Reaction equation

HRID 1350088 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][NH:9][CH2:8][CH:7]2[CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>CN(C=O)C.O>[CH2:26]([N:9]1[CH2:8][CH:7]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([O:3][CH3:2])[CH:5]=2)[CH2:10]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21094293HCID 21094293, compound

Product 1

HCID 11439168HCID 11439168, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

The compound obtained in Example 4 (740 mg; 2.5 mmol) and potassium carbonate (720 mg; 5 mmol) are suspended in 20 ml of DMF, and then benzyl bromide (0.37 ml; 3 mmol) is added to the solution. The reaction mixture is heated at 125° C. for 4 hours with stirring. The solution is poured into 50 ml of water, acidified with 6N HCl and washed with ethyl acetate. The aqueous phase is then rendered alkaline with potassium carbonate and extracted with dichloromethane. The organic phase is dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue so obtained is purified by chromatography on silica gel (eluant: dichloromethane with the progressive addition of methanol until the proportions 9/1 are reached). The purified oil precipitates. The precipitate so formed is recrystallised from a 7/3 toluene/cyclohexane mixture to yield the title product in the form of a white solid.

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue so obtained
  7. customis purified by chromatography on silica gel (eluant
  8. additiondichloromethane with the progressive addition of methanol until the proportions 9/1
  9. customThe purified oil precipitates
  10. customThe precipitate so formed
  11. customis recrystallised from a 7/3 toluene/cyclohexane mixture

Sources & evidence

ORD record
ord-067de3cc67454cdfac93049401280980
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

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