m-Chloroperbenzoic acid → 3-(N-tert.-butoxycarbonylamino)-2-methyl-2,3-epoxypropane
Reaction equation
ClC1C=C[CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.[C:12]([O:16][C:17]([NH:19]C=C(C)C)=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(Cl)(Cl)Cl>[C:12]([O:16][C:17]([NH:19][CH:8]1[O:10][C:4]1([CH3:3])[CH3:5])=[O:18])([CH3:15])([CH3:14])[CH3:13]Participants
Procedure
A solution of 27.18 g of m-chloroperbenzoic acid in chloroform is cooled to circa 10° under argon and treated, by dropwise addition, with a chloroform solution of 17.1 g of 3-(N-tert.-butoxycarbonylamino)-2-methyl-prop-2-ene over a period of 1 hour maintaining the temperature below 15° with external cooling. About 30 minutes after the addition is complete and a white precipitate begins to form. Completeness of the reaction can be judged by chromatographic analysis. When the reaction is complete, the suspension is diluted with chloroform and washed with 3×300 ml of a 10% aqueous solution of sodium bisulphite followed by 3×300 ml of a 10% aqueous solution of sodium bicarbonate. Drying of the organic layer and removal of the solvent in vacuo afforded 3-(N-tert.-butoxycarbonylamino)-2-methyl-2,3-epoxypropane as a colourless oil; 1H-NMR (CDCl3): δ (ppm)=3.3 (2H, t, CH2N), 2.65 (2H, ABq, CH2) 1.43 (9H, s, tBu), 1.33 (3H, s, CH3).
Workup
- temperaturemaintaining the temperature below 15° with external cooling
- additionAbout 30 minutes after the addition
- customto form
- customCompleteness of the reaction
- washwashed with 3×300 ml of a 10% aqueous solution of sodium bisulphite
- customDrying of the organic layer and removal of the solvent in vacuo
Sources & evidence
- ORD record
- ord-08873e6aba8b4ebcb023a2d47265520f
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05190934
Reaction notes
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