Ammonia → HCID 57331350, compound

Temperature

-45 °C

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.

1. customover a time interval of several minutes
2. customthe deep blue reaction
3. customwas quenched with solid ammonium chloride
4. temperaturewarmed slowly to room temperature
5. additionWater (3 mL) was then added to the reaction flask
6. extractionthe mixture extracted with methylene chloride (3×30 mL)
7. customThe combined organic layer was dried
8. concentrationconcentrated in vacuo

ORD record

ord-db91c288a16c4b5193e29e1d32a89df7

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200011B2