Potassium Carbonate → (3-Cyano-3-butene-1-yl)(ethoxycarbonyl)azanyl 1,1-dimethylethyl carbonate
Reaction equation
CS(O[CH2:6][CH2:7][CH:8]([CH2:11]O)[C:9]#[N:10])(=O)=O.[C:13](=[O:26])([O:19][NH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])ON(C(C)(C)C)C(OCC)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:13](=[O:26])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[O:19][N:20]([CH2:6][CH2:7][C:8]([C:9]#[N:10])=[CH2:11])[C:21]([O:23][CH2:24][CH3:25])=[O:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 4-methylsulfonyloxy-2-(hydroxymethyl) butanenitrile (i.e. the product of Step E) (6.87 g, 0.039 mol), 1,1-dimethylethyl (ethoxycarbonyl)azanyl carbonate (7.65 g, 0.037 mol) (i.e. the product of Step F) and potassium carbonate (10.21 g, 0.074 mol) in N,N-dimethylformamide (50 mL) was stirred at room temperature for 20 h. The reaction mixture was poured onto iced water (100 mL) and extracted with diethyl ether (3×50 mL). The combined organic layers were washed with water (50 mL) and concentrated to a pale-tan oil (10.05 g). The oil was adsorbed onto Celite® (diatomaceous filter aid), and then purified by silica gel chromatography (0-100% gradient of ethyl acetate in petroleum ether as eluant). The appropriate fractions were combined to provide the title compound as a yellow oil (3.78 g).
Workup
- extractionextracted with diethyl ether (3×50 mL)
- washThe combined organic layers were washed with water (50 mL)
- concentrationconcentrated to a pale-tan oil (10.05 g)
- custompurified by silica gel chromatography (0-100% gradient of ethyl acetate in petroleum ether as eluant)
Sources & evidence
- ORD record
- ord-b33f2e5e72ee4041adbf8b4167d0f42f
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835427B2
Reaction notes
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