Azetidine → HCID 68002628, compound

HRID 1051850Notes

Reaction equation

HRID 1051850 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].[NH:19]1[CH2:22][CH2:21][CH2:20]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[N:19]1([C:6]([C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([O:11][CH3:12])[CH:4]=2)=[O:8])[CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 10422AzetidineHCID 11430Potassium CarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 162158674-Bromo-3-methoxybenzoic acid

Product 1

HCID 68002628HCID 68002628, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromo-3-methoxybenzoic acid (400 mg) in DMF (4.0 mL) was added potassium carbonate (720 mg), azetidine (148 mg) and TBTU (890 mg). The mixture was stirred at room temperature for 60 h. Water was added, the mixture was stirred for 15 minutes and the solvent was removed in vacuum. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 370 mg of the title compound.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. customthe solvent was removed in vacuum
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with saturated sodium chloride solution
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-874ad71fef814229b7e907e08c031447
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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