1,2-Dichloroethane → HCID 59382925, compound

Participants

Reaction Steps

A mixture of (S)-2-(tert-butoxycarbonylamino)-3-(4-methylcyclohexyl)propanoic acid (2.080 g, 7.29 mmol, 1.0 equiv), EDC (3.308 g, 2.37 equiv), HOBT (1.752 g, 1.78 equiv), DIEA (7.6 mL, 6 equiv) and 33% wt. methylamine in EtOH (2.771 g, 4 equiv) in CH2Cl2 (80 mL) was stirred at rt for 21 h. The solvents were removed in vacuo and 200 mL of 1 N HCl was added. The mixture was extracted three times with EtOAc, washed with brine, and dried over Na2SO4. After the solvents were removed in vacuo, the residue was purified by reversed-phase HPLC to give 1.0167 g (47%) of (S)-tert-butyl 1-(methylamino)-3-(4-methylcyclohexyl)-1-oxopropan-2-ylcarbamate. MS ESI +ve m/z 321 (M+Na). 1H NMR (CDCl3, 400 MHz) δ 6.27 (br s, 1H), 4.91 (br s, 1H), 4.11-4.07 (m, 1H), 2.80, 2.79 (d, J=4.8 Hz, 3H), 1.85-1.20 (m, 21H), 0.88, 0.85 (d, J=6.4 Hz, 3H).

Provenance & Evidence