(4S,8R,10aS)-4-Amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((4S,8R,10aS)-5-oxo-8-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Participants

Reaction Steps

(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((4S,8R,10aS)-5-oxo-8-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate was synthesized as described in General Procedure H using Intermediate 23 (15 mg, 0.026 mmol) and Intermediate 61 (8.5 mg, 0.032 mmol) to give a white solid (16 mg, 73% yield). Anal. Calcd. for C41H51F3N4O6S2 m/z 816.4. found: 817.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.43 (d, J=7.0 Hz, 1H), 7.36 (d, J=7.0 Hz, 1H), 7.30-7.06 (m, 10H), 5.33 (t, J=4.5 Hz, 1H), 5.26 (t, 1H), 5.12-5.06 (m, 1H), 5.00 (qd, J=10.2, 3.2 Hz, 2H), 4.47 (dd, J=13.4, 4.5 Hz, 1H), 3.68 (s, 3H), 3.17-3.03 (m, 2H), 2.89 (dd, J=15.3, 10.4 Hz, 2H), 2.84-2.70 (m, 5H), 2.55 (ddd, J=14.5, 5.9, 2.9 Hz, 1H), 2.49-2.38 (m, 3H), 2.38-2.24 (m, 1H), 2.16-1.99 (m, 4H), 1.99-1.86 (m, 1H), 1.83-1.45 (m, 11H), 1.22 (td, J=11.0, 8.0 Hz, 1H).

Provenance & Evidence