1,1'-Carbonyldiimidazole → tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[Cl-].[CH3:28][O:29][NH2+:30][CH3:31].C(N(C(C)C)CC)(C)C>CCOCC.O1CCCC1>[CH3:28][O:29][N:30]([CH3:31])[C:12]([CH:10]1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:11]1)=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a 100 ml round bottom flask was added 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (3.75 g, 18.6 mmol) and 20 ml tetrahydrofuran, followed by CDI (3.63 g, 22.4 mmol). Vigorous gas evolution was observed. After gas evolution stopped, the reaction mixture was stirred at room temperature for additional 30 minutes. Methoxy(methyl)ammonium chloride (2.55 g, 26.1 mmol) was added, followed by diisopropylethyl amine (6.5 ml, 37.3 mmol). The resulting reaction mixture was stirred at room temperature overnight. It was diluted with 120 ml ether and washed with 60 ml saturated NH4Cl. The organics were dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel column, eluted with 1:2 to 3:2 ethyl acetate/hexane to give 3.6 g desired product was colorless oil.
Workup
- customThe resulting reaction mixture
- stirringwas stirred at room temperature overnight
- washwashed with 60 ml saturated NH4Cl
- dry with materialThe organics were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified on silica gel column
- washeluted with 1:2 to 3:2 ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-d8b6efe02de34818bbbe789cc411540e
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304434B2
Reaction notes
Loading…