(4S,7S,10aS)-methyl 7-amino-6-oxodecahydropyrido[1,2-a]azepine-4-carboxylate → Dimethyl (4S,7S,10aS,4'S,7'S,10a'S)-7,7'-(((2R,5R)-2,5-dibenzyl-1,6-dioxo-1,6-hexanediyl)diimino)bis(6-oxodecahydropyrido[1,2-a]azepine-4-carboxylate)

HRID 529571Notes

Reaction equation

HRID 529571 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H](CC1C=CC=CC=1)C(O)=O)[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][C@@H:26]1[C:32](=[O:33])[N:31]2[C@H:34]([C:38]([O:40][CH3:41])=[O:39])[CH2:35][CH2:36][CH2:37][C@@H:30]2[CH2:29][CH2:28][CH2:27]1>>[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([NH:25][C@@H:26]1[C:32](=[O:33])[N:31]2[C@H:34]([C:38]([O:40][CH3:41])=[O:39])[CH2:35][CH2:36][CH2:37][C@@H:30]2[CH2:29][CH2:28][CH2:27]1)=[O:10])[C:9]([NH:25][C@@H:26]1[C:32](=[O:33])[N:31]2[C@H:34]([C:38]([O:40][CH3:41])=[O:39])[CH2:35][CH2:36][CH2:37][C@@H:30]2[CH2:29][CH2:28][CH2:27]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10610081(4S,7S,10aS)-methyl 7-amino-6-oxodecahydropyrido[1,2-a]azepine-4-carboxylateHCID 68292409(2R,5R)-2,5-dibenzylhexanedioic acid

Product 1

HCID 68310540Dimethyl (4S,7S,10aS,4'S,7'S,10a'S)-7,7'-(((2R,5R)-2,5-dibenzyl-1,6-dioxo-1,6-hexanediyl)diimino)bis(6-oxodecahydropyrido[1,2-a]azepine-4-carboxylate)

Procedure

Dimethyl (4S,7S,10aS,4′S,7′S,10a′S)-7,7′-(((2R,5R)-2,5-dibenzyl-1,6-dioxo-1,6-hexanediyl)diimino)bis(6-oxodecahydropyrido[1,2-a]azepine-4-carboxylate) was synthesized as described in General Procedure F using Intermediate 3 (10 mg, 0.031 mmol) and (4S,7S,10aS)-methyl 7-amino-6-oxodecahydropyrido[1,2-a]azepine-4-carboxylate (16 mg, 0.067 mmol) to give a white solid (8.0 mg, 34% yield). Anal. Calcd. for C44H58N4O8 m/z 770.5. found: 771.5 (M+H)+.

Sources & evidence

ORD record
ord-0ccb70643575472da5e964b7d8e4b30b
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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