Acetone → HCID 178431949, compound

Participants

Reaction Steps

To a slurry of dry acetone (5 ml.) and 6-triphenylmethylamino-2,2-dimethyl-3-(5-tetrazolyl)penam (483 mg., 1.0 mmole) at room temperature is added p-toluenesulfonic acid monohydrate (209 mg., 1.1 mmole). The resulting solution is stirred for 10 minutes, and then ether (30 ml.) is added over a five minute period. The mixture is stirred for ten minutes after which the solvent is decanted from the residue. The residue is dissolved in tetrahydrofuran (30 ml.) and placed on a column (300 × 6 mm.) packed with 10 g. of Florisil (snythetic magnesium silicate). The column is eluted with tetrahydrofuran until a total of 125 ml. is collected. The eluate is concentrated to dryness under reduced pressure at 40° C. to give 210 mg. of solid. The solid is slurried in ether (30 ml.), filtered, washed with ether and air-dried. Yield = 121 mg. (50%). NMR (DMSO-d6): 5.88 (s, 3H), -- 5.10 (s, 3H) 5.52 (d, 1H), 4.60 (d, 2H), 1.59 (s, 3H) and 1.08 ppm (s, 3H).

Provenance & Evidence