(2R,5R)-2,5-Dibenzyl-6-((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-6-oxohexanoic acid → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((7S,10aR)-6-oxodecahydropyrido[1,2-a]azepin-7-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529604Notes

Reaction equation

[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:15]([NH:17][C@H:18]1[CH2:24][CH2:23][S:22][C@H:21]2[CH2:25][CH2:26][CH2:27][C@@H:28]([C:29]([O:31][CH3:32])=[O:30])[N:20]2[C:19]1=[O:33])=[O:16])[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:42][C@@H:43]1[C:49](=[O:50])[N:48]2[CH2:51][CH2:52][CH2:53][CH2:54][C@@H:47]2[CH2:46][CH2:45][CH2:44]1>>[CH2:34]([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](=[O:11])[NH:42][C@@H:43]1[C:49](=[O:50])[N:48]2[CH2:51][CH2:52][CH2:53][CH2:54][C@@H:47]2[CH2:46][CH2:45][CH2:44]1)[C:15]([NH:17][C@H:18]1[CH2:24][CH2:23][S:22][C@H:21]2[CH2:25][CH2:26][CH2:27][C@@H:28]([C:29]([O:31][CH3:32])=[O:30])[N:20]2[C:19]1=[O:33])=[O:16])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Reactant 2

HCID 68311179(2R,5R)-2,5-Dibenzyl-6-((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-6-oxohexanoic acid

HCID 86706215(7S,10aR)-7-aminooctahydropyrido[1,2-a]azepin-6(7H)-one hydrochloride

Product 1

HCID 66546277(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((7S,10aR)-6-oxodecahydropyrido[1,2-a]azepin-7-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Procedure

(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((7S,10aR)-6-oxodecahydropyrido[1,2-a]azepin-7-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate was synthesized as described in General Procedure H using Intermediate 23 (11 mg, 0.019 mmol) and Intermediate 54 (4.7 mg, 0.021 mmol) to give a white solid (12 mg, 91% yield). Anal. Calcd. for C41H54N4O6S m/z 730.4. found: 731.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.32-7.07 (12H, m), 5.33 (1H, t, J=4.7 Hz), 5.15-5.08 (1H, m), 5.05-4.95 (1H, m), 4.83-4.72 (1H, m), 4.15 (1H, d, J=11.5 Hz), 3.88-3.77 (1H, m), 3.68 (3H, s), 3.15 (1H, ddd, J=14.2, 11.1, 2.7 Hz), 2.90-2.68 (6H, m), 2.51-2.35 (3H, m), 2.08-1.99 (2H, m), 1.85-1.42 (20H, m), 1.06-0.90 (1H, m).

Sources & evidence

ORD record: ord-fb2b259723194bea817988a350b5f070
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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