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

HRID 529584Notes

Reaction equation

HRID 529584 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][CH2:41][CH2:42][CH3:43])=[O:39])[N:29]2[C:28]1=[O:44]>>[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][CH2:41][CH2:42][CH3:43])[N:29]2[C:28]1=[O:44])=[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][CH2:41][CH2:42][CH3:43])[N:29]2[C:28]1=[O:44])=[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 68292610(4S,7S,10aS)-4-Amino-5-oxo-N-propyloctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxamide hydrochloride salt

Product 1

HCID 86706245(2R,5R)-2,5-Dibenzyl-N1,N6-bis((4S,7S,10aS)-5-oxo-7-(propylcarbamoyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

Procedure

(2R,5R)-2,5-Dibenzyl-N1,N6-bis((4S,7S,10aS)-5-oxo-7-(propylcarbamoyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide was synthesized as described in General Procedure F using Intermediate 3 (7.9 mg, 0.024 mmol) and Intermediate 38 (18 mg, 0.056 mmol) to give a light yellow solid (15 mg, 70% yield). Anal. Calcd. for C46H64N6O6S2 m/z 860.7. found: 861.6 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.24-7.13 (m, 10H), 5.31 (m, 2H), 4.94 (m, 4H), 3.33-3.13 (m, 6H), 2.76 (m, 6H), 2.35 (m, 4H), 2.08 (m, 4H), 1.70-1.47 (m, 18H), 0.90 (m, 6H).

Sources & evidence

ORD record
ord-740df1cf60ed4e7f96060de5f9ea4ca4
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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