(4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrile → (2R,5R)-2,5-Dibenzyl-N1-((4S,7S,10aS)-7-cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((S)-2-oxo-1-o-tolylazepan-3-yl)hexanediamide

HRID 529632Notes

Reaction equation

HRID 529632 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:15](=[O:32])[NH:16][C@H:17]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[C:18]1=[O:31])[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:40][C@H:41]1[CH2:47][CH2:46][S:45][C@H:44]2[CH2:48][CH2:49][CH2:50][C@@H:51]([C:52]#[N:53])[N:43]2[C:42]1=[O:54]>>[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:15]([NH:16][C@H:17]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[C:18]1=[O:31])=[O:32])[C:9]([NH:40][C@H:41]1[CH2:47][CH2:46][S:45][C@H:44]2[CH2:48][CH2:49][CH2:50][C@@H:51]([C:52]#[N:53])[N:43]2[C:42]1=[O:54])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 68292315(4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrileHCID 68292933(2R,5R)-2,5-Dibenzyl-6-oxo-6-((S)-2-oxo-1-o-tolylazepan-3-ylamino)hexanoic acid

Product 1

HCID 86706263(2R,5R)-2,5-Dibenzyl-N1-((4S,7S,10aS)-7-cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((S)-2-oxo-1-o-tolylazepan-3-yl)hexanediamide

Procedure

(2R,5R)-2,5-Dibenzyl-N1-((4S,7S,10aS)-7-cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((S)-2-oxo-1-o-tolylazepan-3-yl)hexanediamide was synthesized as described in General Procedure H using Intermediate 71 (10 mg, 0.019 mmol) and Intermediate 36 (5.2 mg, 0.020 mmol) to give a white solid (8.0 mg, 57% yield). Anal. Calcd. for C43H51N5O4S m/z 733.7. found: 734.3 (M+H)+; 1H NMR (400 MHz, CDCl3) (Rotamers) δ ppm 7.39-6.79 (16H, m), 5.35 (1H, d, J=3.8 Hz), 5.24 (1H, d, J=4.9 Hz), 5.02-4.90 (1H, m), 4.87-4.77 (1H, m), 4.07-3.88 (1H, m), 3.58-3.29 (1H, m), 3.02-2.86 (1H, m), 2.85-2.70 (4H, m), 2.66-2.36 (3H, m), 2.21-2.09 (5H, m), 2.05-1.47 (14H, m), 1.46-1.15 (2H, m).

Sources & evidence

ORD record
ord-d16b5d98d45f4ca2a7df96fcc71b2d79
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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