Acetone → HCID 86596955, compound

Participants

Reaction Steps

To a solution of (1R,2S,5R)-5-amino-2-(2-(3-tert-butyl-4-hydroxybenzamido)acetamido)cyclohexanecarboxylic acid (67 mg, 0.17 mmol) in anhyd CH2Cl2 (1 mL) and acetone (1 mL) was added acetic acid (0.5 mL) and NaBH(OAc)3 (110 mg, 0.51 mmol) and the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2 (1 mL) and CH3CN (1 mL). To this solution was added formaldeyde (4 mL, 37% in water) and NaBH(OAc)3 (200 mg, 0.84 mmol) in five portions over 10 h. The reaction mixture was stirred at room temperature for 12 h and then concentrated in vacuo to dryness. The residue was dissolved in water and purified by semi-preparative HPLC to give (1R,2S,5R)-2-(2-(3-tert-butyl-4-hydroxybenzamido)acetamido)-5-(isopropyl(methyl)amino)cyclohexanecarboxylic acid (22.4 mg, 29% over 3 steps) as a white powder: 1H NMR (300 MHz, CD3OD) δ 7.95 (s, 1H), 7.78 (s, 1H), 7.58-7.54 (m, 1H), 6.80-6.77 (m, 1H), 4.55 (s, 1H), 4.08-3.91 (m, 3H), 3.90-3.71 (m, 1H), 3.69-3.45 (m, 1H), 2.92-2.85 (m, 1H), 2.79 (s, 3H), 2.15-1.55 (m, 7H), 1.41-1.33 (m, 15H); MS found: (M+H)+=448.

Provenance & Evidence