Diisopropylethylamine → HCID 11611023, compound

Participants

Reaction Steps

To a solution of Example 17D (32 mg, 0.1 mmol) in anhydrous THF (5 mL) was added N,N-diisopropylethylamine (0.035 mL, 0.2 mmol) followed by 4-chlorosulfonyl-benzoic acid (20.92 mg, 0.12 mmol). The mixture was stirred for 8 hours at room temperature and concentrated under reduced pressure. The residue was taken up in anhydrous dichloromethane (3 mL) and trifluoroacetic acid (0.075 mL) in dichloromethane (0.075 mL) was added and the mixture was allowed to stir for 5 hours at room temperature. The mixture was concentrated under reduced pressure and purified using RP-HPLC to provide the titled compound. MS (ESI) m/e 400 (M+H)+, 398 (M−H)−; 1H NMR (500 MHz, CD3OD) δ ppm 1.78 (m, 1 H) 2.65 (m, 1 H) 3.00 (m, 2 H) 3.08 (m, 1 H) 3.14 (m, 1 H) 3.20 (m, 1 H) 3.49 (m, 1 H) 3.60 (m, 1 H) 3.73 (m, 1H) 3.88 (m, 1 H) 4.50 (m, 1 H) 4.66 (m, 2 H) 7.95 (d, 2 H) 8.19 (d, 2 H).

Provenance & Evidence