HCID 58813159, compound → (1S,4R,5S,8S,14R)-5-Benzyl-4-hydroxy-8-((S)-3-isobutyl-2-oxo-pyrrolidin-1-yl)-18-methoxy-13-oxa-2,6-diaza-tricyclo[12.6.1.015,20]henicosa-10,15(20),16,18-tetraen-7-one

Participants

Reaction Steps

Hoveyda-Grubb's 2nd generation catalyst (3.01 mg, 3.55 μmol) was added to flask charge with a solution of (S)—N-((2S,3R)-4-((1S,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-yl)-2-((S)-3-isobutyl-2-oxopyrrolidin-1-yl)pent-4-enamide (25.5 mg, 35.5 μmol, TFA salt) from step 0 (1) in DCM (4 mL) at RT. The mixture was stirred for 16 h. Evaporated to dryness. Dissolved in MeOH and filtered. Purified with reverse phase Prep-HPLC to give 17.9 mg (75%) of the (1S,4R,5S,8S,14R)-5-Benzyl-4-hydroxy-8-((S)-3-isobutyl-2-oxo-pyrrolidin-1-yl)-18-methoxy-13-oxa-2,6-diaza-tricyclo[12.6.1.015,20]henicosa-10,15(20),16,18-tetraen-7-one as the TFA salt: LC-MS (M+H)+=576.2, HRMS (M+H)+=576.3447; 1H NMR (500 MHz, CDCl3) 8 ppm 0.91 (dd, J=32.81, 5.95 Hz, 4H) 1.11 (t, J=9.77 Hz, 1H) 1.30-1.44 (m, 1H) 1.55-1.72 (m, 2H) 2.03 (dd, J=13.12, 4.58 Hz, 2H) 2.28-2.76 (m, 12H) 3.14 (s, 3H) 3.72-3.92 (m, 3H) 4.04-4.19 (m, 2H) 4.40 (s, 1H) 4.72 (d, J=4.58 Hz, 1H) 4.83-4.96 (m, 1H) 5.51-5.74 (m, 1H) 6.92-7.30 (m, 8H) 7.35 (t, J=8.39 Hz, 1H).

Provenance & Evidence