Water → HCID 18765857, compound

HRID 481010Notes

Reaction equation

HRID 481010 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]1[NH:18][C:19]([CH2:39][C:40]([O:42][CH3:43])=[O:41])=[C:20]([C:35]([O:37][CH3:38])=[O:36])[CH:21]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:34])[C:22]=1[C:23]([O:25][CH3:26])=[O:24])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Cl:34][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([Cl:33])[C:27]=1[CH:21]1[C:20]([C:35]([O:37][CH3:38])=[O:36])=[C:19]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[NH:18][C:17]([CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])=[C:22]1[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 69943569HCID 69943569, compound

Product 1

HCID 18765857HCID 18765857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 2-[2-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethyl]-4-(2,6-dichlorophenyl)-6-(2-methoxy-2-oxoethyl)-1,4-dihydro-3,5-pyridinedicarboxylate (example 5, 3.90 g/6.01 mmol) in THF (39 ml) was added a solution of tetrabutylammonium fluoride (6.0 ml/6.0 mmol) at 0° C. and the resulting solution was stirred for 30 min at room temperature. The mixture was poured into water. The whole was extracted with dichloromethane (100 ml×2). The combined organic layer was washed with brine (30 ml), dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography (SiO2, 200-350 mesh/hexane:ethyl acetate=4:1-2:1) to afford a yellow oil (3.20 g/99%).

Workup

  1. extractionThe whole was extracted with dichloromethane (100 ml×2)
  2. washThe combined organic layer was washed with brine (30 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (SiO2, 200-350 mesh/hexane:ethyl acetate=4:1-2:1)
  7. customto afford a yellow oil (3.20 g/99%)

Sources & evidence

ORD record
ord-709340c229b74964b84dc12901864fcc
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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