Diisopropylethylamine → HCID 68759365, compound

Participants

Reaction Conditions

Reaction Steps

To a 500 ml flask was added methyl 6-(pyridin-4-yl)indoline-4-carboxylate 54.1.C (1.98 g, 7.81 mmole), of HBTU (5.92 g, 15.6 mmole), (S)-2-(tert-butoxycarbonyl)-3-phenylpropanoic acid 3.11 g, 11.7 mmole, available from Aldrich) 50 ml of DMF and DIEA (4.08 ml, 23.4 mmole). The reaction was stirred at 60° C. for 6 hours, at which time the crude reaction was partitioned between 1000 ml of EtAc and 500 ml of water. The solvent was removed and the crude purified using a silica gel column (Elutent; 50/50 EtAc/Hex) to give (S)-methyl 1-(2-(tert-butoxycarbonyl)-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxylate 54.1.D as a yellow solid (2.05 g, 52.3% yield).

Provenance & Evidence