Trifluoroacetic acid → HCID 66546087, compound

Participants

Reaction Steps

TFA (0.1 mL) was added to a 0° C. solution of methyl (4S,7S,10aS)-4-(((2R,5R)-2-benzyl-8-tert-butoxy-5-(((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepin-4-yl)carbamoyl)-8-oxooctanoyl)amino)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (45 mg, 0.053 mmol) in DCM (0.2 mL). The reaction mixture was then stirred at rt for 4 hr. The reaction mixture was concentrated and dried under vacuum. The residue was purified by RP prep-HPLC to give (4R,7R)-7-benzyl-8-((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-4-((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamoyl)-8-oxooctanoic acid (8.5 mg, 0.011 mmol, 20% yield) as a white solid. Anal. Calcd. for C38H52N4O10S2 m/z 788.5. found: 789.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.59 (1H, d, J=5.5 Hz), 7.29-7.10 (6H, m), 5.44-5.29 (2H, m), 5.24-4.96 (6H, m), 3.72 (3H, s), 3.69 (3H, s), 3.30-3.19 (1H, m), 3.18-3.08 (1H, m), 2.97-2.68 (4H, m), 2.50-2.17 (6H, m), 2.10-1.91 (5H, m), 1.90-1.54 (11H, m), 1.53-1.39 (2H, m).

Provenance & Evidence