Diisopropylethylamine → HCID 86641223, compound

Participants

Reaction Steps

To a stirred solution of N-methyl-4-phenoxyaniline (110 mg, 0.55 mmol) in anh THF (10 mL) under Ar was added triphosgene (60 mg, 0.20 mmol) in one portion at 0° C. followed by DIPEA (0.1 mL, 0.58 mmol). The reaction was stirred at the temperature for 10 min and then at rt for 2 h. At this time, the reaction was cooled and treated with (R)-2-amino-4-(benzyloxy)-N,N-dimethyl-4-oxobutan-1-aminium 2,2,2-trifluoroacetate (193 mg, 0.55 mmol) in anh THF (6 mL) at 0° C. followed by DIPEA (0.3 mL, 1.7 mmol). The reaction was allowed to slowly warm to rt overnight. The mixture was then concentrated under reduced pressure and purified by preparative TLC (SiO2, 20% MeOH/DCM) to afford the title compound as a light yellow oil (129 mg, 51%). 1H NMR (400 MHz, CD3OD) δ ppm 7.22-7.42 (m, 8 H), 7.08-7.19 (m, 3 H), 7.00-7.06 (m, 2 H), 6.90-6.95 (m, 2 H), 5.05-5.20 (m, 2 H), 4.50-4.62 (m, 1 H), 3.19 (s, 3 H), 2.99-3.17 (m, 2 H), 2.86 (s, 6 H), 2.50-2.71 (m, 2 H). MS ESI [M+H]+, calcd for [C27H31N3O4+H]+: 462.56 found m/z 462.3 (100).

Provenance & Evidence