Benzyl Bromide → HCID 58975516, compound

HRID 1178778Notes

Reaction equation

HRID 1178778 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:18])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:9]1=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 21974600194611-73-9

Product 1

HCID 58975516HCID 58975516, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1A (95 mg, 0.36 mmol) in DMF (2 mL) was added Cs2CO3 (260 mg, 0.8 mmol), followed by benzyl bromide (74 mg, 0.43 mmol). After stirring at RT under argon for 4 h, the mixture was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (20 mL). The combined organic layers were washed with brine, dried (Na2SO4), and evaporated under vacuum. The resulting residue was chromatographed on silica gel (10 g) eluted with 20-30% EtOAc in hexane (step-wise gradient) to obtain the title compound (112 mg, 88%).

Workup

  1. customthe mixture was partitioned between water and EtOAc
  2. extractionThe aqueous layer was extracted with EtOAc (20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated under vacuum
  6. customThe resulting residue was chromatographed on silica gel (10 g)
  7. washeluted with 20-30% EtOAc in hexane (step-wise gradient)

Sources & evidence

ORD record
ord-11a57db231a0449f8bdf2527678f1c84
Source dataset
uspto-grants-2007_10
Patent number
US07276608B2

Reaction notes

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