Diisopropylethylamine → HCID 86706343, compound

Participants

Reaction Steps

To a solution of 1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid 91.52 g, 6.1 mmol) and DIPEA (3.15 g, 24.4 mmol) in DMF (8 mL) was added (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)hexanoyl fluoride (10) (1.7 g, 6.1 mmol) in DMF. The reaction mixture was stirred at rt overnight and LC/MS indicated completion of the reaction. The mixture was diluted with ethyl acetate (20 mL), and washed with 5% aqueous citric acid, brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:1) followed by DCM/MeOH (200:1) to provide the title compound (0.48 g, 32%). LCMS: (M+H)+: 512.0. 1H NMR (300 MHz, CDCl3) δ ppm 0.79 (t, J=6.0 Hz, 3H), 1.10 (m, 4H), 1.40 (m, 1H), 1.57 (m, 1H), 1.77 (m, 1H), 2.17 (m, 1H), 2.97 (m, 2H), 3.25-3.69 (m, 1H), 4.13 (m, 3H), 4.56-4.93 (m, 2H), 5.12 (s, 2H), 7.34 (m, 10H), 7.74 (s, 0.3H), 8.36 (s, 0.6H).

Provenance & Evidence