(4S,8R,10aS)-4-Amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one → (2R,5R)-2,5-Dibenzyl-N1-((S)-2-oxo-1-phenylazepan-3-yl)-N6-((4S,8R,10aS)-5-oxo-8-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

HRID 529609Notes

Reaction equation

HRID 529609 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:15](=[O:31])[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][CH:25]=2)[C:18]1=[O:30])[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:39][C@H:40]1[CH2:46][CH2:45][S:44][C@H:43]2[CH2:47][CH2:48][C@@H:49]([C:51]([F:54])([F:53])[F:52])[CH2:50][N:42]2[C:41]1=[O:55]>>[CH2:32]([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:39][C@H:40]1[CH2:46][CH2:45][S:44][C@H:43]2[CH2:47][CH2:48][C@@H:49]([C:51]([F:52])([F:54])[F:53])[CH2:50][N:42]2[C:41]1=[O:55])=[O:10])[C:15]([NH:16][C@H:17]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]1=[O:30])=[O:31])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 68292539(4S,8R,10aS)-4-Amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-oneHCID 86706193(2R,5R)-2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoic acid

Product 1

HCID 86706252(2R,5R)-2,5-Dibenzyl-N1-((S)-2-oxo-1-phenylazepan-3-yl)-N6-((4S,8R,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-phenylazepan-3-yl)-N6-((4S,8R,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 24 (15 mg, 0.029 mmol) and Intermediate 61 (9.4 mg, 0.035 mmol) to give a white solid (14 mg, 63% yield). Anal. Calcd. for C42H49F3N4O4S m/z 762.4. found: 763.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.45-7.02 (m, 15H), 5.24 (t, 1H), 5.02-4.90 (m, 1H), 4.79 (dd, J=9.4, 7.0 Hz, 1H), 4.48 (dd, J=13.3, 4.4 Hz, 1H), 3.94 (dd, J=16.1, 12.3 Hz, 1H), 3.60 (d, J=15.1 Hz, 1H), 3.11-3.00 (m, 1H), 2.93-2.68 (m, 5H), 2.52 (ddd, J=14.4, 6.0, 2.9 Hz, 1H), 2.48-2.21 (m, 4H), 2.17-1.46 (m, 13H), 1.42-1.09 (m, 4H).

Sources & evidence

ORD record
ord-99199bc6a85e4f9c84b1f1cef09b220f
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

Loading…