3,5-Dimethylaniline → HCID 28213684, compound

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Reaction Steps

This compound is an intermediate for the synthesis of the compound of example 6. To the solution of N-Boc-L-alanine (1.000 g, 5.28 mmol) in dichloromethane (10 ml) is added dicyclohexylcarbodiimide (DCC, 1,094 g, 5.28 mmol) in dichloromethane (10 ml). To this mixture is added 3,5-dimethylaniline (0.640 g, 5.28 mmol) in dichloromethane (10 ml). After 16 h of mixing at room temperature, the dicyclohexylurea is recovered on a filter, the filtrate is dry evaporated. 1.41 g (91%) of white powder are obtained, mp 134°–136° C. The material is dissolved in trifluoroacetic acid (5 ml) and the solution is mixed for 30 min. at room temperature. The solution is dry evaporated. The product is dissolved in methanol (10 ml). To this solution dichloromethane (30 ml) is added and the solution is washed with a solution of 1 M (30 ml) sodium carbonate and water (2×30 ml). The organic phase is dry evaporated. 0.64 g (63%) of product are obtained in the form of a brown oil.

Provenance & Evidence