Trifluoroacetic acid → HCID 86747172, compound

Participants

Reaction Steps

To 1-dimethylacrylamido-12-BOC-amino-4,9-dioxadodecane (0.6 g, 1.6 mmole) in a 25 ml round bottom flask was added 10 ml of freshly distilled thiolacetic acid. The solution was stirred and refluxed under nitrogen for four hours. The solution was cooled and diluted to 70 ml with diethyl ether. The ether solution was washed with water, 5% acetic acid, water, and saturated sodium chloride solution, and dried over magnesium sulfate. Concentration gave a pale brown oil: 1-(3-acetylthio-3-methylbutyramido)-12-BOC-amino-4,9-dioxadodecane (4). This crude product was stirred with 5 ml trifluoroacetic acid for 1/2 hour at room temperature. The TFA was removed by evaporation with a stream of nitrogen. Yield (crude product)=0.59 g (1.6 mmole, ~100%) of 1-(3-acetylthio-3-methylbutyramido-12-amino-4,9-dioxadodecane (5).

Provenance & Evidence