Potassium Carbonate → HCID 69882706, compound

HRID 353375Notes

Reaction equation

HRID 353375 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2([CH:11]3[CH2:12][C:8]4([C:13]([OH:15])=[O:14])[CH:9]([CH2:10]3)[CH:7]24)[C:4](=[O:16])[NH:3]1.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:14][C:13]([C:8]23[CH2:12][CH:11]4[C:5]5([C:4](=[O:16])[N:3]([CH2:22][C:21]6[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=6)[C:2](=[O:1])[N:6]5[CH2:22][C:21]5[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=5)[CH:7]2[CH:9]3[CH2:10]4)=[O:15])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 12151259HCID 12151259, compound

Product 1

HCID 69882706HCID 69882706, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1.1 g (5.0 mmole) of 2′,5′-dioxo-spiro{tricyclo[2.2.1.02,6]heptane-3,4′-imidazoline}-1-carboxylic acid in 30 mL of N,N-dimethylformamide was treated with an excess of p-fluorobenzyl bromide (4.73 g, 25 mmole) and potassium carbonate (3.45 g, 25 mmole) at 60° C. for 36 hours. After cooling to room temperature, the mixture was diluted to 500 mL with water and extracted with 2×250 mL of ethyl acetate. The extracts were washed with water, dried over sodium sulfate and concentrated in vacuum to give 2.7 g of the title compound, again as a mixture of diastereomers.

Workup

  1. extractionextracted with 2×250 mL of ethyl acetate
  2. washThe extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-e376614fc0084054ad69eb4f9ec42cfb
Source dataset
uspto-grants-2004_06
Patent number
US06750364B2

Reaction notes

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