Methanol → HCID 71711673, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-tert-butoxy-2-(4-(4-fluorophenyl)-2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)acetic acid (example 1) (10 mg, 0.023 mmol) in CH2Cl2 (5 mL) was added Et3N (0.020 mL, 0.140 mmol) and the resulting mixture cooled to 0° C. Added to this was 2-(4-methylphenylsulfonamido)-3-phenylpropanoyl chloride (23.65 mg, 0.070 mmol) and the mixture stirred at room temperature (mixture became a clear colorless solution over time). After 1 h, 0.5 mL MeOH was added and the mixture was concentrated under a stream of air and taken up in MeOH and purified by preparative HPLC (10% AcCN/90% H2O/0.1% NH4OAc, Sunfire 19×100 mm, C18, 5 μm column) The product-containing fractions were concentrated to remove the organic solvent and the resulting precipitate was collected by filtration to give 2-tert-butoxy-2-(4-(4-fluorophenyl)-2-isopropyl-8,8-dimethyl-6-(2-(4-methylphenylsulfonamido)-3-phenylpropanoyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)acetic acid (3.7 mg, 21% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 7.56-7.80 (1H, m), 6.91-7.57 (12H, m), 6.71-6.92 (1H, m), 4.85 (1H, s), 3.99-4.26 (1H, m), 3.78-4.00 (0.5H, m), 3.46-3.77 (1.5H, m), 3.36-3.46 (2H, m), 3.13-3.28 (1H, m), 2.60-2.87 (2H, m), 2.11-2.50 (3H, m), 0.85-1.46 (21H, m). 19F NMR (400 MHz, CD3OD) δ ppm −114.16, −115.11, −117.98, −118.41. LCMS (M+H) calcd for C41H49FN3O6: 730.33. found: 730.03.

Provenance & Evidence