Ammonia → HCID 57331350, compound

Participants

Reaction Conditions

Reaction Steps

A cold (−50° C.) solution of (1S,2S)—N-(tert-butyl)-1-(N—((S)-1-phenylethyl) acetamido)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)cyclopentane carboxamide (0.400 g, 0.802 mmol) in anhydrous tetrahydrofuran (5 mL) under an inert atmosphere of nitrogen was gradually combined (in small portions), with liquid ammonia (20 mL) and lithium wire (0.14 g, 20 mmol) over a time interval of several minutes. After stirring for 1.5 h at −40 to −50° C., the deep blue reaction was quenched with solid ammonium chloride, warmed slowly to room temperature, and residual ammonia driven off using nitrogen. Water (3 mL) was then added to the reaction flask and the mixture extracted with methylene chloride (3×30 mL). The combined organic layer was dried using Na2SO4 and concentrated in vacuo prior to purifification by HPLC to afford the subject compound (100 mg, 50%) as a white foam. NMR (D2O) δ 2.32 (m, 1 H), 2.00 (m, 2 H), 1.77-1.90 (m, 2 H), 1.70 (m, 1 H), 1.35-1.50 (m, 3 H), 1.24 (m, 1 H), 1.12 (m, 1 H), 0.60-0.75 (m, 2 H). MS (M+1): 216.3; MS (M−H2O+1): 198.2; MS (M−2H2O+1): 180.3.

Provenance & Evidence