1,2-Dichloroethane → HCID 88924275, compound

Participants

Reaction Steps

EDC (2.01 g, 10.51 mmol) was added in one portion to a solution of (2R,3R)-3-((tert-butoxycarbonyl)amino)-2-ethylbutanoic acid (1.62 g, 7.00 mmol), (S)-methyl 2-amino-3-hydroxypropanoate hydrochloride (1.64 g, 10.51 mmol), HOBT (1.61 g, 10.51 mmol) and triethylamine (3.42 ml, 24.51 mmol) in anhydrous dichloromethane (28.0 ml). The reaction mixture was allowed to stir at rt under a nitrogen atmosphere overnight before evaporating in vacuo. The residue was then taken up in ethyl acetate (50 mL) and washed with water (50 mL). The organic was then dried (MgSO4) and evaporated in vacuo. The residue was treated with MeOH to precipitate title compound (1.71 g, 74%) which was used immediately in the next reaction. 1H NMR (400 MHz, CCl3D) δ 6.56 (d, J=6.6 Hz, 1H), 4.68 (dt, J=7.2, 3.5 Hz, 1H), 4.09-3.98 (m, 2H), 3.98-3.91 (m, 1H), 3.86 (br. s., 1H), 3.81 (s, 3H), 1.83-1.67 (m, 1H), 1.67-1.52 (m, 1H), 1.44 (s, 9H), 1.18 (d, J=6.8 Hz, 3H), 0.96 (t, J=7.5 Hz, 3H).

Provenance & Evidence