HCID 89691337, compound → HCID 89691366, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl N-(4-[[(3R)-3-[(2R)-2-[(tert-butyldimethylsilyl)oxy]-2-carbamoylethyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-ethylcarbamate (200 mg, 0.32 mmol, 1.00 equiv), hydrogen chloride(conc.) (0.3 mL) in dichloromethane (3 mL). The resulting solution was stirred for 1 h at 0° C. The resulting mixture was concentrated under vacuum. The crude product (200 mg) was purified by preparative HPLC under the following conditions (1#-Pre-HPLC-016(Waters)): column: SunFire Prep C18, 19*150 mm 5 um; mobile phase: water WITH 50 mL NH4CO3 and CH3CN (5.0% CH3CN up to 44.5.0% in 10 min, up to 95.0% in 2 min, down to 5.0% in 2 min); detector: 254/220 nm. 57.4 mg product was obtained. This resulted in 57.4 mg (44%) of (2R)-3-[(3R)-12-[[4-(ethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]-2-hydroxypropanamide as a white solid. MS: m/z 405 (M+H)+. 1H-NMR (300 MHz, CD3OD): δ 8.474 (1H, s), 5.25-5.22 (1H, m), 4.00-4.03 (1H, t), 3.61 (1H, m), 3.07-3.10 (1H, m), 2.94-2.98 (1H, m), 2.52-2.68 (4H, m), 2.18-2.39 (2H, m), 1.64-1.71 (3H, m), 1.26-1.34 (2H, m), 1.08-1.13 (3H, d).

Provenance & Evidence