Hydrochloric Acid → HCID 19813415, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[CH:18])[CH:12]=2)[C:9]([C:19]([O:21][CH3:22])=[O:20])=[C:8]([CH3:23])[NH:7][C:6]=1[CH:24](OC)[O:25]C)=[O:4].Cl>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[CH:18])[CH:12]=2)[C:9]([C:19]([O:21][CH3:22])=[O:20])=[C:8]([CH3:23])[NH:7][C:6]=1[CH:24]=[O:25])=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The mixture of 4.3 g (0.011 mol) of 3,5-dimethoxycarbonyl-1,4-dihydro-6-methyl-2-dimethoxymethyl-4-(3 -ethynylphenyl)pyridine obtained in Example 14, 5 ml of 6N hydrochloric acid and 50 ml of acetone was stirred for 4 hours at room temperature. After completing the reaction, acetone was distilled away, water was added to the residue. Then pH of the solution was adjusted to 7.5 with saturated solution of sodium hydrogencarbonate. The solution was extracted with ethyl acetate several times. All organic layers thereof were mixed, and were washed with water, dehydrated and concentrated. Then, the residue was purified by subjecting to silica gel column chromatography [eluent: benzene-ethyl acetate (5 : 4)] and recrystallized from ethyl acetate to give 2.4 g of the desired compound as yellow prism crystals (yield: 64.9%).
Workup
- distillationwas distilled away
- additionwater was added to the residue
- extractionThe solution was extracted with ethyl acetate several times
- additionAll organic layers thereof were mixed
- washwere washed with water
- concentrationconcentrated
- customThen, the residue was purified
- customrecrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-1c38a95c538f41bd85d86aa7620263a9
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05158963
Reaction notes
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