p-Toluenesulfonic acid → HCID 131736625, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 72D (220 mg, 0.521 mmol), pTsOH (194 mg, 1.020 mmol) in CH2Cl2 (100 mL) was degassed by bubbling Ar through for 10 mins and heated at 40° C. for 10 mins. Then, Grubbs II (190 mg, 0.224 mmol) in 3 ml Ar degassed DCM was added dropwise via a syringe pump under Ar, heated at 40° C. for a total of 24 hrs. The reaction mixture was neutralized with sat. aq. NaHCO3 and the organic phase separated and washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by prep HPLC and the desired fractions neutralized with conc. NaHCO3, concentrated to small volume, extracted with EtOAc, dried over MgSO4, filtered and concentrated to yield the desired product as a white solid (15 mg, 7.3%). 1H NMR (400 MHz, METHANOL-d4) δ 8.65 (dd, J=11.4, 5.1 Hz, 2H), 8.54 (s, 1H), 7.60 (d, J=5.1 Hz, 1H), 7.37 (dd, J=5.1, 1.5 Hz, 1H), 6.99 (s, 1H), 5.76 (ddd, J=15.3, 10.6, 4.7 Hz, 1H), 4.68 (dd, J=11.2, 3.5 Hz, 1H), 4.41 (dd, J=15.2, 9.5 Hz, 1H), 3.18 (dq, J=9.3, 6.7 Hz, 1H), 2.78 (ddd, J=8.4, 7.3, 3.9 Hz, 1H), 2.04 (q, J=11.4 Hz, 1H), 1.47 (s, 9H), 1.10 (d, J=6.8 Hz, 3H).

Provenance & Evidence