(2R,5R)-2,5-Dibenzyl-6-oxo-6-((S)-2-oxo-1-o-tolylazepan-3-ylamino)hexanoic acid → (2R,5R)-2,5-Dibenzyl-N1-((S)-2-oxo-1-o-tolylazepan-3-yl)-N6-((4S,8S,10aS)-5-oxo-8-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

HRID 529626Notes

Reaction equation

HRID 529626 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][C@H:50]([C:52]([F:55])([F:54])[F:53])[CH2:51][N:43]2[C:42]1=[O:56]>>[CH2:33]([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:40][C@H:41]1[CH2:47][CH2:46][S:45][C@H:44]2[CH2:48][CH2:49][C@H:50]([C:52]([F:53])([F:55])[F:54])[CH2:51][N:43]2[C:42]1=[O:56])=[O:10])[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:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 68292933(2R,5R)-2,5-Dibenzyl-6-oxo-6-((S)-2-oxo-1-o-tolylazepan-3-ylamino)hexanoic acidHCID 86706221(4S,8S,10aS)-4-amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

Product 1

HCID 86706260(2R,5R)-2,5-Dibenzyl-N1-((S)-2-oxo-1-o-tolylazepan-3-yl)-N6-((4S,8S,10aS)-5-oxo-8-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

Procedure

(2R,5R)-2,5-Dibenzyl-N1-((S)-2-oxo-1-o-tolylazepan-3-yl)-N6-((4S,8S,10aS)-5-oxo-8-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide was synthesized as described in General Procedure H using Intermediate 71 (8.2 mg, 0.016 mmol) and Intermediate 60 (3.5 mg, 0.013 mmol) to give a white solid (5.9 mg, 58% yield). Anal. Calcd. for C43H51F3N4O4S m/z 776.7. found: 777.6 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.42-6.89 (m, 14H), 5.86 (s, 2H), 5.11 (dd, J=14.2, 7.0 Hz, 1H), 4.81 (dd, J=10.6, 6.6 Hz, 2H), 4.38-4.26 (m, 1H), 4.09-3.86 (m, 2H), 3.54 (d, J=16.2 Hz, 1H), 3.40-3.09 (m, 3H), 2.91-2.38 (m, 7H), 2.21 and 2.14 (s, 3H), 2.28-2.07 (m, 1H), 2.07-1.77 (m, 5H), 1.75-1.22 (m, 9H).

Sources & evidence

ORD record
ord-e9a8f80c4b9e45839c645bce807fcef5
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

Loading…