(4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate → Dimethyl (4S,7S,10aS,4'S,7'S,10a'S)-4,4'-(((2S,3E,5S)-2,5-dibenzyl-1,6-dioxo-3-hexene-1,6-diyl)diimino)bis(5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate)

HRID 529570Notes

Reaction equation

HRID 529570 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C@H:19]1[CH2:25][CH2:24][S:23][C@H:22]2[CH2:26][CH2:27][CH2:28][C@@H:29]([C:30]([O:32][CH3:33])=[O:31])[N:21]2[C:20]1=[O:34]>>[CH2:1]([C@@H:14](/[CH:13]=[CH:12]/[C@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([NH:18][C@H:19]1[CH2:25][CH2:24][S:23][C@H:22]2[CH2:26][CH2:27][CH2:28][C@@H:29]([C:30]([O:32][CH3:33])=[O:31])[N:21]2[C:20]1=[O:34])=[O:11])[C:15]([NH:18][C@H:19]1[CH2:25][CH2:24][S:23][C@H:22]2[CH2:26][CH2:27][CH2:28][C@@H:29]([C:30]([O:32][CH3:33])=[O:31])[N:21]2[C:20]1=[O:34])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 10563170(4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylateHCID 68292602(R)-2-Benzylhexanedioic acid

Product 1

HCID 68309843Dimethyl (4S,7S,10aS,4'S,7'S,10a'S)-4,4'-(((2S,3E,5S)-2,5-dibenzyl-1,6-dioxo-3-hexene-1,6-diyl)diimino)bis(5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate)

Procedure

Methyl (4S,7S,10aS)-4-(2R)-2-benzyl-6-(((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepin-4-yl)amino)-6-oxohexanoyl)amino)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate was synthesized as described in General Procedure F using Intermediate 4 (15 mg, 0.061 mmol) and (4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (34.9 mg, 0.135 mmol) to give a white solid (25 mg, 56% yield). Anal. Calcd. for C35H48N4O8S2 m/z 716.6. found: 717.6 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.62 (1H, d, J=6.8 Hz), 7.40 (1H, d, J=7.3 Hz), 7.29-7.22 (2H, m), 7.21-7.11 (3H, m), 5.37 (1H, t, J=4.6 Hz), 5.33 (1H, t, J=4.4 Hz), 5.18-5.07 (3H, m), 5.07-5.00 (1H, m), 3.73 (3H, s), 3.69 (3H, s), 3.29-3.19 (1H, m), 3.18-3.09 (1H, m), 2.93 (1H, ddd, J=14.4, 6.4, 2.7 Hz), 2.87-2.73 (3H, m), 2.56-2.48 (1H, m), 2.48-2.36 (2H, m), 2.36-2.26 (2H, m), 2.25-2.17 (1H, m), 2.09-1.93 (5H, m), 1.82-1.48 (12H, m).

Sources & evidence

ORD record
ord-ff9964c5b5e143fea3965364d2d6c479
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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