Tetrahydrofuran → HCID 72311189, compound

HRID 1157950Notes

Reaction equation

HRID 1157950 reaction equation
[CH3:1][O:2][C:3](=[O:43])[N:4]=[C:5]([S:41][CH3:42])[C:6](=[N:24][C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[C:27]([CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:26]=1)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]([O:15][Si](C(C)(C)C)(C)C)[C:8]=1[F:23].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O>[CH3:1][O:2][C:3](=[O:43])[N:4]=[C:5]([S:41][CH3:42])[C:6](=[N:24][C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[C:27]([CH2:32][NH:33][C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH:26]=1)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]([OH:15])[C:8]=1[F:23]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 72311200HCID 72311200, compound

Product 1

HCID 72311189HCID 72311189, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of {2-[4-bromo-3-(t-butoxycarbonylaminomethyl)phenylimino)-2-[3-(t-butyldimethylsilanyloxy)-5-ethyl-2-fluorophenyl]-1-methylsulfanylethylidene}carbamic acid methyl ester (686 mg) and THF (25 mL) there was added a 1M THF solution (1.18 mL) of tetrabutylammonium fluoride at 0° C., under a nitrogen atmosphere. The mixture was stirred at 0° C. for 2 hours, and then ethyl acetate (200 mL) and water (100 mL) were added. The mixture was sufficiently shaken, and then the organic layer was separated off, washed twice with water (100 mL) and then with saturated aqueous sodium chloride (100 mL) in that order, and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (542 mg) as a colorless solid.

Workup

  1. stirringThe mixture was sufficiently shaken
  2. customthe organic layer was separated off
  3. washwashed twice with water (100 mL)
  4. dry with materialwith saturated aqueous sodium chloride (100 mL) in that order, and dried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customto obtain a filtrate
  7. distillationthe solvent in the filtrate was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture)

Sources & evidence

ORD record
ord-afc0e07a9cce4c739b08c07687f6f69f
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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