Hydrochloric Acid → HCID 59386565, compound

Participants

Reaction Steps

A mixture of (2R,6S,13aS,14aR,16aS,Z)-2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-methoxy-8-(2-nitrophenylsulfonyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[n]pyrrolo[2,1-c][1,4,8]triazacyclopentadecine-14a-carboxylic acid (13 mg, 0.016 mmol) and CDI (3.61 mg, 0.022 mmol) in tetrahydrofuran (2 mL) was refluxed for 1 h. It was then cooled to rt and cyclopropanesulfonamide (2.70 mg, 0.022 mmol) was added followed by DBU (8.39 μL, 0.056 mmol). The reaction mixture was stirred at rt 18 h, and then it was concentrated in vacuo to yield a light yellow oil. To this oil was added 5 mL of water, adjusting to pH=4 using 1N HCl. The white precipitate was collected by filtration and washed with water to give 15 mg of the crude product as a white solid. Purification by flash chromatography eluting with 2% MeOH/CH2Cl2 gave 8 mg of tert-butyl (2R,6S,13aS,14aR,16aS,Z)-2-(biphenyl-4-yl)-14a-(cyclopropylsulfonylcarbamoyl)-2-methoxy-8-(2-nitrophenylsulfonyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[n]pyrrolo[2,1-c][1,4,8]triazacyclopentadecin-6-ylcarbamate as a white solid. LC-MS: MS m/z 889(M+1-MeOH). (This product was contaminated with an equal portion of the P1 methyl ester by-product.)

Provenance & Evidence