Hydrochloric Acid → Ammonium Hydroxide

Participants

Reaction Steps

Potassium trimethylsilanoate (1.21 g, 9.45 mmol) was added to a stirred suspension of methyl 1-{[(3S)-3-amino-3-phenylpropyl]amino}cyclopentanecarboxylate bis-hydrochloride (1.00 g, 2.86 mmol, Intermediate 38) in THF (5.0 mL) at ambient temperature. After 4 h, the reaction mixture was adjusted to pH=8 with aqueous 1 M HCl. To this mixture was added HOAt (0.195 g, 1.43 mmol), and EDCI (0.549 g, 2.87 mmol). After 1 h, the reaction was concentrated in vacuo. The residue was partitioned between CH2Cl2 and water. The aqueous phase was extracted several times with CH2Cl2. The combined organic extracts were washed with saturated brine, then dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with CH2Cl2:MeOH:NH4OH—89.9:10:0.1 to give the title compound. MS: m/z=245 (M+1).

Provenance & Evidence