Citric Acid → HCID 68584691, compound

HRID 17618Notes

Reaction equation

HRID 17618 reaction equation
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([C:15](=[CH2:25])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:4]=1[CH3:32])#[N:2].[CH2:33](Br)[CH:34]=[CH2:35].[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH2:35]([N:17]([CH2:16][C:15]([C:6]1[C:7]2[O:11][C:10]([CH:12]3[CH2:14][CH2:13]3)=[N:9][C:8]=2[C:3]([C:1]#[N:2])=[C:4]([CH3:32])[C:5]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[CH2:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:34]=[CH2:33]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 86630885tert-Butyl [2-(4-cyano-2-Cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)prop-2-en-1-yl]carbamate

Product 1

HCID 68584691HCID 68584691, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl [2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)prop-2-en-1-yl]carbamate (I-325) (97.0 mg, 0.226 mmol) and allyl bromide (28.7 μl, 0.339 mmol) were dissolved in dimethylformamide (2 ml), then with cooling with ice, sodium hydride (55% w/w) (11.8 mg, 0.271 mmol) was added, followed by stirring for 2 hours with cooling with ice. With cooling with ice, aqueous 10% citric acid solution was added to the reaction liquid, followed by concentration under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:1, v/v) to obtain the entitled compound (105 mg, 99%) as a colorless oily substance.

Workup

  1. additionwas added
  2. temperaturewith cooling with ice
  3. additionwas added to the reaction liquid
  4. concentrationfollowed by concentration under reduced pressure
  5. dissolutionThe resulting residue was dissolved in ethyl acetate
  6. washwashed with water and saturated brine
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. customthe insoluble matter was separated by filtration
  9. customthe residue obtained by concentration
  10. customwas purified by silica gel column chromatography (eluent, n-hexane

Sources & evidence

ORD record
ord-afeb7f795e2c44d591788a2973624089
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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