Imidazole → HCID 59383062, compound

Participants

Reaction Steps

To a solution of the (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-hydroxycyclohexyl)propanoate (96.56 g, 0.32 mol) in CH2Cl2 (500 mL) was added imidazole (43.52 g, 0.64 mol), followed by TBSCl (72 g, 0.48 mol) at 0° C. After addition, the mixture was allowed to stir at rt overnight. The reaction mixture was treated with water and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered, and evaporated to give (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(tert-butyldimethylsilyloxy)cyclohexyl)propanoate (133 g, yield 100%). 1H NMR: (CDCl3, 400 MHz) δ 0.08 (d, 6H), 0.89 (d, 9H), 1.45 (s, 9H), 1.51 (m, 4H), 1.58 (m, 1H), 1.68 (t, 4H), 1.85 (d, 1H), 3.71 (d, 3H), 3.91 (m, 1H), 4.34 (m, 1H), 4.86 (m, 1H).

Provenance & Evidence