Benzyl Bromide → HCID 57907595, compound

HRID 887116Notes

Reaction equation

HRID 887116 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:25]([O:17][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[N:9]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 57907411HCID 57907411, compound

Product 1

HCID 57907595HCID 57907595, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 60.0 g (236 mmol) of 4-[1-(tert-butoxycarbonyl)-1H-pyrazol-3-yl]butanoic acid from step C above in 400 mL of DMF was added 48.9 g (354 mmol) of potassium carbonate followed by dropwise addition of 40.0 mL (300 mmol) of benzyl bromide. The resulting mixture was stirred for 24 h, quenched with water, and extracted with ethyl acetate (3×300 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The crude residue was purified by silica gel chromatography eluting with 30% ethyl acetate in hexanes to afford the title compound as a yellow oil (55.6 g. 68.4%). LC-MS: m/z (ES) 345 (MH)−.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate (3×300 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customThe crude residue was purified by silica gel chromatography
  8. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3a2b48e06615439a9fb293558cfba7ab
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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