Water → HCID 67529778, compound

HRID 17851Notes

Reaction equation

HRID 17851 reaction equation
[C:1]([C:4]1[CH:18]=[CH:17][C:7]2[N:8]([CH:14]3[CH2:16][CH2:15]3)[CH2:9][NH:10][S:11](=[O:13])(=[O:12])[C:6]=2[CH:5]=1)([OH:3])=[O:2].[C:19]1(O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1CCN2C(=NCCC2)CC1.O>CN(C=O)C>[CH:14]1([N:8]2[C:7]3[CH:17]=[CH:18][C:4]([C:1]([O:3][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[O:2])=[CH:5][C:6]=3[S:11](=[O:13])(=[O:12])[NH:10][CH2:9]2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67531156HCID 67531156, compound

Product 1

HCID 67529778HCID 67529778, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N′-carbonyldiimidazole (0.6 g) is added to a solution of the compound of Example 78 (3.5 mmol) in DMF (7 mL). After stirring for 1 hour at ambient temperature, phenol (0.5 g) and DBU (0.5 mL) are added. After stirring for 2 hours at ambient temperature, water (40 mL) is added and the mixture is extracted three times with ethyl acetate (30 mL). The organic phases are combined, dried over anhydrous MgSO4 and filtered. The filtrate is evaporated to dryness and the residue is re-dissolved in methanol (5 mL). Water (50 mL) is added to the solution and the precipitate obtained is collected by filtration, washed with water and dried to yield the title product in the form of a white solid.

Workup

  1. stirringAfter stirring for 2 hours at ambient temperature
  2. extractionthe mixture is extracted three times with ethyl acetate (30 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe filtrate is evaporated to dryness
  6. dissolutionthe residue is re-dissolved in methanol (5 mL)
  7. additionWater (50 mL) is added to the solution
  8. customthe precipitate obtained
  9. filtrationis collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-b130f9db0c61482b9afc54def67a0f9b
Source dataset
uspto-grants-2010_06
Patent number
US07741320B2

Reaction notes

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