Water → HCID 68733618, compound

HRID 884061Notes

Reaction equation

HRID 884061 reaction equation
[CH3:1][N:2]([CH3:46])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:45])/[C:14](/[C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][O:43][CH3:44])=[CH:37][CH:36]=2)=[C:15](/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)\[CH2:16][CH2:17][O:18][Si](C(C)C)(C(C)C)C(C)C)=[CH:8][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH3:46][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:45])/[C:14](/[C:35]2[CH:36]=[CH:37][C:38]([O:41][CH2:42][O:43][CH3:44])=[CH:39][CH:40]=2)=[C:15](/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)\[CH2:16][CH2:17][OH:18])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 68732418HCID 68732418, compound

Product 1

HCID 68733618HCID 68733618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5f (95 mg, 0.147 mmol) in THF (2 ml) was added a 1M solution of tetrabutylammonium fluoride (0.18 ml) in THF under ice cooling, and the mixture was stirred at room temperature for 30 min. H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. Purification by silica gel flash column chromatography (eluent: AcOEt to CHCl3/MeOH, 5:1) gave 5 g (90%). 5 g: colorless oil; 1H-NMR (CDCl3) δ 2.74 (2H, t, J=5.7 Hz), 3.02 (2H, t, J=5.6 Hz), 3.43 (3H, s), 3.63 (2H, t, J=5.6 Hz), 4.06 (2H, t, J=5.7 Hz), 5.09 (2H, s), 6.79 (2H, d, J=8.3 Hz), 6.88 (2H, d, J=9.1 Hz), 6.99 (2H, d, J=8.6 Hz), 7.09 (2H, m), 7.16-7.21 (3H, m), 7.45 (2H, d, J=8.8 Hz), 7.82 (1H, brs).

Workup

  1. extractionthe whole was extracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by silica gel flash column chromatography (eluent: AcOEt to CHCl3/MeOH, 5:1)
  6. customgave 5 g (90%)

Sources & evidence

ORD record
ord-6dfa1ba96c7542a38f1bc0902c2f4a93
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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