Water → HCID 67062570, compound

Participants

Reaction Steps

To a 25 mL of round-bottom flask was added allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate (68 mg, 230 μmol) (prepared as shown for Example 11), 1,8-diazabicyclo(5.4.0)-7-undecene (6.8 μl, 46 μmol) and 2 mL of DMF at room temperature. (S)-3-((1-(4-Nitrophenylsulfonyl)aziridin-2-yl)methyl)-1H-indole (98 mg, 276 μmol) (prepared as described in US Patent Publication No. US 2007/0173506 which is hereby incorporated by reference in its entirety and for all purposes as if specifically set forth herein) in 1 mL of DMF was added to the reaction mixture dropwise. After 3 hours, 10 mL of water was added, and then the reaction mixture was extracted twice with 20 mL of EtOAc. The extracts were combined, concentrated under reduced pressure, and purified by flash chromatography on silica gel (65% EtOAc/hexane) to give allyl(S)-3-(1H-indol-3-yl)-2-(4-nitrophenylsulfonamido)propyl(3-(isoquinolin-6-yl)isoxazol-5-yl)carbamate (130 mg, 86% yield). MS m/z: 653 (M+1).

Provenance & Evidence