Water → HCID 19434880, compound

HRID 1736227Notes

Reaction equation

HRID 1736227 reaction equation
C(OC([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[C:24]([F:25])=[C:23]([CH2:26][O:27][C:28](=[O:34])[N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[C:22]([F:35])=[C:21]([NH2:36])[C:17]=3[C:18](=[O:20])[CH:19]=2)=[CH:10][C:9]=1[F:37])=O)C=C.C(N(CC)CC)C.C(O)=O.O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:36][C:21]1[C:17]2[C:18](=[O:20])[CH:19]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([NH2:7])=[C:9]([F:37])[CH:10]=3)[O:15][C:16]=2[C:24]([F:25])=[C:23]([CH2:26][O:27][C:28](=[O:34])[N:29]([CH2:30][CH3:31])[CH2:32][CH3:33])[C:22]=1[F:35]

Participants

6

Reactant 3

HCID 962WaterHCID 11084032Triethylammonium formateHCID 19434940HCID 19434940, compound

Product 1

HCID 19434880HCID 19434880, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

223 mg (0.429 mmol) of the above 2-(4-allyloxycarbonylamino-3-fluorophenyl)-5-amino-7-diethylcarbamoyloxymethyl-6,8-difluoro-4H-1-benzopyran-4-one was dissolved in 20 mL of tetrahydrofuran, 0.29 mL of formic acid-triethylamine and 50 mg (0.043 mmol) of tetrakis(triphenylphosphine)palladium were added and the mixture was stirred at room temperature for 40 minutes. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) and recrystallized from ethyl acetate/n-hexane, to give 105 mg of Compound 156 (yield: 56%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform)
  6. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-884c5134db8e4d66b64052a4e5fcdc22
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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