Water → HCID 67521476, compound

HRID 1926165Notes

Reaction equation

HRID 1926165 reaction equation
C([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]1[C:23]2[C:22]([NH:24][C:25]3[CH:44]=[CH:43][C:28]([O:29][C:30]4[CH:42]=[CH:41][C:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:32][CH:31]=4)=[C:27]([Cl:45])[CH:26]=3)=[N:21][CH:20]=[N:19][C:18]=2[CH:17]=[CH:16]1)(=O)C1C=CC=CC=1.O>CO.O1CCCC1.[OH-].[Na+]>[ClH:45].[Cl:45][C:27]1[CH:26]=[C:25]([NH:24][C:22]2[C:23]3[N:15]([CH2:14][CH2:13][O:12][CH2:11][CH2:10][OH:9])[CH:16]=[CH:17][C:18]=3[N:19]=[CH:20][N:21]=2)[CH:44]=[CH:43][C:28]=1[O:29][C:30]1[CH:42]=[CH:41][C:33]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])=[CH:32][CH:31]=1

Participants

6

Reactant 2

HCID 962WaterHCID 67521544HCID 67521544, compound

Product 1

HCID 67521476HCID 67521476, compoundYield 193.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

tert-Butyl 4-{4-[(5-{2-[2-(benzoyloxy)ethoxy]ethyl}-5H-pyrrolo[3,2-d]pyrimidin-4-yl)amino]-2-chlorophenoxy}benzoate (189 mg) was dissolved in a mixed solvent of methanol (5 mL) and tetrahydrofuran (1 mL), 1N aqueous sodium hydroxide solution (0.6 mL) was added, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was subjected to basic silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→10:90). The object fraction was concentrated under reduced pressure. The residue was dissolved in ethyl acetate-ethanol, and 1N hydrochloric acid/ethyl acetate solution (0.3 mL) was added. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from ethanol-ethyl acetate to give the title compound (163 mg) as a white powder.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe object fraction was concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate-ethanol
  8. addition1N hydrochloric acid/ethyl acetate solution (0.3 mL) was added
  9. customThe solvent was evaporated under reduced pressure
  10. customthe obtained residue was crystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-5f8609c5b921449482875cd8101af179
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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