Tetrahydrofuran → {2-[3-(t-Butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-(5-ethyl-2-fluoro-3-hydroxyphenyl)-1-methylsulfanylethylidene}carbamic Acid Methyl Ester

HRID 1157952Notes

Reaction equation

HRID 1157952 reaction equation
[CH3:1][O:2][C:3](=[O:47])[N:4]=[C:5]([S:45][CH3:46])[C:6](=[N:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[C:30]([CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:29]=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(C)C)[C:8]=1[F:26].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O>[CH3:1][O:2][C:3](=[O:47])[N:4]=[C:5]([S:45][CH3:46])[C:6](=[N:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[C:30]([CH2:36][NH:37][C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[CH:29]=1)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]([OH:15])[C:8]=1[F:26]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 72311201{2-[3-(t-Butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-(5-ethyl-2-fluoro-3-triisopropylsilanyloxyphenyl)-1-methylsulfanylethylidene}carbamic acid methyl ester

Product 1

HCID 72311195{2-[3-(t-Butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-(5-ethyl-2-fluoro-3-hydroxyphenyl)-1-methylsulfanylethylidene}carbamic Acid Methyl EsterYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of {2-[3-(t-butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-(5-ethyl-2-fluoro-3-triisopropylsilanyloxyphenyl)-1-methylsulfanylethylidene}carbamic acid methyl ester (523 mg) and THF (10 mL) there was added a 1M THF solution of tetrabutylammonium fluoride (1.56 mL) under a nitrogen atmosphere. The mixture was stirred for 90 minutes, and then ethyl acetate (300 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 once 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 (346 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) and once with saturated aqueous sodium chloride (100 mL) in that order
  4. dry with materialdried 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-2b9215bb5fab4d659983f01b763bac00
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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