(3S)-3-Aminohexahydro-1-(2-phenylethyl)-2H-azepin-2-one → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S)-2-oxo-1-phenethylazepan-3-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529591Notes

Reaction equation

HRID 529591 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](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:41][C@H:42]1[CH2:48][CH2:47][CH2:46][CH2:45][N:44]([CH2:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:43]1=[O:57]>>[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:10])[NH:41][C@H:42]1[CH2:48][CH2:47][CH2:46][CH2:45][N:44]([CH2:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:43]1=[O:57])[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

3

Reactant 2

HCID 68291941(3S)-3-Aminohexahydro-1-(2-phenylethyl)-2H-azepin-2-oneHCID 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

Product 1

HCID 66548769(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S)-2-oxo-1-phenethylazepan-3-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-((S)-2-oxo-1-phenethylazepan-3-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 (7.0 mg, 0.012 mmol) and (S)-3-amino-1-phenethylazepan-2-one (2.9 mg, 0.012 mmol) to give a white solid (2.0 mg, 20% yield). Anal. Calcd. for C45H56N4O6S m/z 780.7. found: 781.7 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 7.31-7.27 (m, 2H), 7.24-7.19 (m, 6H), 7.18-7.10 (m, 7H), 6.91 (d, J=6.60 Hz, 1H), 6.86 (d, J=6.60 Hz, 1H), 5.32 (t, J=4.95 Hz, 1H), 5.19-5.09 (m, 1H), 5.04-4.92 (m, 1H), 4.50 (dd, J=9.89, 6.60 Hz, 1H), 3.73-3.69 (m, 1H), 3.68 (s, 3H), 3.53-3.39 (m, 2H), 3.24-3.03 (m, 2H), 2.86-2.77 (m, 5H), 2.76-2.67 (m, 2H), 2.43-2.32 (m, 3H), 2.06-1.97 (m, 2H), 1.91-1.83 (m, 2H), 1.79-1.47 (m, 13H).

Sources & evidence

ORD record
ord-8f910251d9494d048063cb40d73bbe8c
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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