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

HRID 529621Notes

Reaction equation

HRID 529621 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][CH2:22][CH2:21][N:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])[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][S:46][C@H:45]2[CH2:49][CH2:50][CH2:51][C@H:52]([C:53]([F:56])([F:55])[F:54])[N:44]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]([NH:41][C@H:42]1[CH2:48][CH2:47][S:46][C@H:45]2[CH2:49][CH2:50][CH2:51][C@H:52]([C:53]([F:54])([F:56])[F:55])[N:44]2[C:43]1=[O:57])=[O:10])[C:15]([NH:17][C@H:18]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])[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 68292507(4S,7R,10aS)-4-Amino-7-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-oneHCID 68310532(2R,5R)-2,5-dibenzyl-6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylamino)-6-oxohexanoic acid

Product 1

HCID 86706256(2R,5R)-2,5-Dibenzyl-N1-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)-N6-((4S,7R,10aS)-5-oxo-7-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

Procedure

(2R,5R)-2,5-Dibenzyl-N1-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)-N6-((4S,7R,10aS)-5-oxo-7-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide was synthesized as described in General Procedure H using Intermediate 70 (21 mg, 0.039 mmol) and Intermediate 78 (10 mg, 0.037 mmol) to give a white solid (26 mg, 83% yield). Anal. Calcd. for C43H51F3N4O5S m/z 792.7. found: 793.4 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.37-6.99 (m, 12H), 6.99-6.86 (m, 3H), 6.77 (s, 1H), 5.27 (t, 1H), 5.02-4.80 (m, 2H), 4.75 (dd, J=10.2, 6.6 Hz, 1H), 3.96-3.81 (m, 1H), 3.80 (s, 3H), 3.38 (s, 1H), 3.24-3.07 (m, 1H), 2.91-2.46 (m, 7H), 2.36 (dd, J=12.8, 8.4 Hz, 4H), 2.14-1.58 (m, 9H), 1.58-1.20 (m, 5H).

Sources & evidence

ORD record
ord-09a8542397ab4b33b27e3cbd2e2d65a5
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

Loading…