(2R,5R)-2,5-dibenzylhexanedioic acid → (2R,5R)-2,5-Dibenzyl-N1-((4R,7S,10aS)-5-oxo-7-(thiazol-2-ylcarbamoyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((4S,7S,10aS)-5-oxo-7-(thiazol-2-ylcarbamoyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

HRID 529583Notes

Reaction equation

HRID 529583 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([OH:17])=O)[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:26][C@H:27]1[CH2:33][CH2:32][S:31][C@H:30]2[CH2:34][CH2:35][CH2:36][C@@H:37]([C:38]([NH:40][C:41]3[S:42][CH:43]=[CH:44][N:45]=3)=[O:39])[N:29]2[C:28]1=[O:46]>>[CH2:18]([C@@H:14]([CH2:13][CH2:12][C@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([NH:26][C@H:27]1[CH2:33][CH2:32][S:31][C@H:30]2[CH2:34][CH2:35][CH2:36][C@@H:37]([C:38](=[O:39])[NH:40][C:41]3[S:42][CH:43]=[CH:44][N:45]=3)[N:29]2[C:28]1=[O:46])=[O:11])[C:15]([NH:26][C@@H:27]1[CH2:33][CH2:32][S:31][C@H:30]2[CH2:34][CH2:35][CH2:36][C@@H:37]([C:38](=[O:39])[NH:40][C:41]3[S:42][CH:43]=[CH:44][N:45]=3)[N:29]2[C:28]1=[O:46])=[O:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 68292409(2R,5R)-2,5-dibenzylhexanedioic acidHCID 86706203(4S,7S,10aS)-4-amino-5-oxo-N-(thiazol-2-yl)octahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxamide hydrochloride salt

Product 1

HCID 86706244(2R,5R)-2,5-Dibenzyl-N1-((4R,7S,10aS)-5-oxo-7-(thiazol-2-ylcarbamoyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((4S,7S,10aS)-5-oxo-7-(thiazol-2-ylcarbamoyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

Procedure

(2R,5R)-2,5-Dibenzyl-N1-((4R,7S,10aS)-5-oxo-7-(thiazol-2-ylcarbamoyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((4S,7S,10aS)-5-oxo-7-(thiazol-2-ylcarbamoyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide was synthesized as described in General Procedure F using Intermediate 3 (10 mg, 0.031 mmol) and Intermediate 37 (25 mg, 0.069 mmol) to give a white solid (14 mg, 46% yield). Anal. Calcd. for C46H54N8O6S4 m/z 942.7. found: 943.5 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.21-7.11 (m, 14H), 5.38 (br s, 2H), 5.11 (m, 4H), 3.15 (m, 2H), 2.76 (m, 6H), 2.36 (m, 4H), 2.12 (m, 4H), 1.85-1.40 (m, 14H).

Sources & evidence

ORD record
ord-94e45b9a7f764a8b80a9eb395fdfc04b
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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