(3R,9aS)-3-Amino-2,2-dimethylhexahydropyrido[2,1-b][1,3]thiazin-4(6H)-one → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((3R,9aS)-2,2-dimethyl-4-oxooctahydropyrido[2,1-b][1,3]thiazin-3-ylamino)-6-oxohexanamido)-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-((3R,9aS)-2,2-dimethyl-4-oxooctahydropyrido[2,1-b][1,3]thiazin-3-ylamino)-6-oxohexanamido)-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 30 (8.7 mg, 0.026 mmol) to give a white solid (12 mg, 56% yield). Anal. Calcd. for C41H54N4O6S2 m/z 762.4. found: 763.4 (M+H)+; 1H NMR (500 MHz, CD3OD) δ ppm 8.09 (d, J=7.70 Hz, 1H), 7.94 (d, J=9.35 Hz, 1H), 7.28-7.06 (m, 10H), 5.54 (dd, J=6.32, 3.02 Hz, 1H), 5.13-5.07 (m, 1H), 5.03 (dd, J=10.17, 3.57 Hz, 1H), 4.82-4.78 (m, 1H), 4.76 (d, J=9.35 Hz, 1H), 4.20 (d, J=13.20 Hz, 1H), 3.63 (s, 3H), 3.14-3.04 (m, 1H), 3.00-2.91 (m, 1H), 2.91-2.76 (m, 4H), 2.77-2.66 (m, 3H), 2.41-2.28 (m, 1H), 2.14-2.03 (m, 1H), 2.02-1.87 (m, 2H), 1.84-1.51 (m, 14H), 0.99 (s, 3H), 0.74 (s, 3H).

Provenance & Evidence