Benzyl Bromide → HCID 17866572, compound

HRID 583345Notes

Reaction equation

HRID 583345 reaction equation
[C:1]([C:3]1[C:4]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[C:5]([CH:9]=[C:10]([CH3:12])[CH:11]=1)[C:6]([OH:8])=[O:7])#[N:2].C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CC(C)=O>[CH2:31]([C:11]1[C:10]([CH3:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C:3]=1[C:1]#[N:2])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 17866683HCID 17866683, compound

Product 1

HCID 17866572HCID 17866572, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.5 g (4.3 mmol) of the product of Example 176 in 200 mL of acetone was added 4 g of K2CO3 and 5 ml of benzylbromide and the mixture was refluxed for 8 hours. The reaction mixture was then filtered and the acetone was removed in vacuo. The residue was dissolved in chloroform and washed well with water. The organic layer was then dried over MgSO4, filtered and concentrated in vacuo. The resulting residue chromatographed on silica gel luting with 30% Ethyl acetateexane to give 1.8 g (79%) of the desired product as a brown oil. Electrospray Mass Spec 527 (M+H).

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. filtrationThe reaction mixture was then filtered
  3. customthe acetone was removed in vacuo
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed well with water
  6. dry with materialThe organic layer was then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue chromatographed on silica gel luting with 30% Ethyl acetateexane

Sources & evidence

ORD record
ord-3af42580fd484a63afa80cc39fa2e0ff
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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