Water → HCID 20637931, compound

HRID 1856690Notes

Reaction equation

HRID 1856690 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[O:7]1[CH:11]=[N:10][N:9]=[C:8]1[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH2:26][C@@H:27]2[CH:32]=COC(=O)[O:28]2)[CH:20]=1.O>CN(C)C=O>[O:7]1[CH:11]=[N:10][N:9]=[C:8]1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:32][C@H:27]([OH:28])[CH2:26][CH2:25][C:21]2[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 7147704-(1,3,4-Oxadiazol-2-yl)phenolHCID 70201731HCID 70201731, compound

Product 1

HCID 20637931HCID 20637931, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Cesium carbonate (0.72 g) and 4-(1,3,4)-oxadiazol-2-yl-phenol (0.54 g) were added to a solution of (4R)-4-[2-(pyridin-3-yl)ethyl]-1,3-dioxin-2-one (1.20 g, Example 14a)) in dry dimethylformamide (75 ml) and heated at 90° C. for 14 hours. After cooling, the reaction mixture was poured into water (50 ml) and extracted three times with ethyl acetate. The combined organic phases were extracted twice with 2M hydrochloric acid. The combined aqueous extracts were basified by dropwise addition of 2M aqueous sodium hydroxide and the aqueous solution was then extracted three times with ethyl acetate. The organic extracts were combined and dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by normal phase HPLC eluting with 0 to 25% ethanol in dichloromethane to give the title compound as a solid (0.19 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with ethyl acetate
  3. extractionThe combined organic phases were extracted twice with 2M hydrochloric acid
  4. additionThe combined aqueous extracts were basified by dropwise addition of 2M aqueous sodium hydroxide
  5. extractionthe aqueous solution was then extracted three times with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by normal phase HPLC
  10. washeluting with 0 to 25% ethanol in dichloromethane

Sources & evidence

ORD record
ord-cf732f4a2ae14380b6f51db8bfd61385
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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