Water → HCID 22086866, compound

HRID 2227374Notes

Reaction equation

HRID 2227374 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[C:13]([CH2:23][N:24]([CH3:32])[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[N:15]=[C:9]2[N:8]([CH2:33][C:34]2[C:39]([F:40])=[CH:38][CH:37]=[CH:36][C:35]=2[F:41])[CH:7]=1)=[O:5])[CH3:2].O.[CH:43](Cl)(Cl)Cl>CC(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[C:13]([CH2:23][N:24]([CH3:32])[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:14]([C:16]3[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=3)[N:15]=[C:9]2[N:8]([CH2:33][C:34]2[C:35]([F:41])=[CH:36][CH:37]=[CH:38][C:39]=2[F:40])[CH:7]=1)=[O:5])([CH3:43])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6212Chloroform2×HCID 15521576HCID 15521576, compound

Product 1

HCID 22086866HCID 22086866, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the compound obtained in Example 12 (0.10 g, 0.18 mmol) in chloroform (5 ml) is added a solution of titanium(IV) isopropoxide (0.3 ml, 1.0 mmol) in 2-propanol (10 ml). Then the mixture is refluxed at 80° C. for 8 hours, successively is stirred at room temperature for 150 minutes. To this mixture is added a mixture of chloroform (50 ml) and water (50 ml). The aqueous layer is extracted with chloroform (20 ml). The combined organic extract is dried over Na2SO4 and concentrated under reduced pressure to give the residue, which is chromatographed on silica gel to afford white-brown crystalline solid, which is recrystallized from chloroform-n-hexane to afford pale brown crystals (0.58 g, 94%).

Workup

  1. additionTo this mixture is added
  2. extractionThe aqueous layer is extracted with chloroform (20 ml)
  3. extractionThe combined organic extract
  4. dry with materialis dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give the residue, which
  7. customis chromatographed on silica gel
  8. customto afford white-brown crystalline solid, which
  9. customis recrystallized from chloroform-n-hexane

Sources & evidence

ORD record
ord-db9620f2ca1c4239a7e7ce7f00e96743
Source dataset
uspto-grants-2002_07
Patent number
US06413972B1

Reaction notes

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