(2R,5S)-2-(4-Fluorobenzyl)-5-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamoyl)octanoic acid → (2R,5S)-2-(4-Fluorobenzyl)-N6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)-N1-((4S,7S,10aS)-5-oxo-7-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-5-propylhexanediamide

HRID 529631Notes

Reaction equation

HRID 529631 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][C@@H:7]([CH2:11][CH2:12][C@@H:13]([C:17](=[O:35])[NH:18][C@H:19]2[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])[C:20]2=[O:34])[CH2:14][CH2:15][CH3:16])[C:8](O)=[O:9])=[CH:4][CH:3]=1.[NH2:38][C@H:39]1[CH2:45][CH2:44][S:43][C@H:42]2[CH2:46][CH2:47][CH2:48][C@@H:49]([C:50]([F:53])([F:52])[F:51])[N:41]2[C:40]1=[O:54]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]([CH2:11][CH2:12][C@H:13]([CH2:14][CH2:15][CH3:16])[C:17]([NH:18][C@H:19]2[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])[C:20]2=[O:34])=[O:35])[C:8]([NH:38][C@H:39]2[CH2:45][CH2:44][S:43][C@H:42]3[CH2:46][CH2:47][CH2:48][C@@H:49]([C:50]([F:51])([F:53])[F:52])[N:41]3[C:40]2=[O:54])=[O:9])=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 68311019(2R,5S)-2-(4-Fluorobenzyl)-5-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamoyl)octanoic acidHCID 86706238(4S,7S,10aS)-4-Amino-7-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

Product 1

HCID 68310558(2R,5S)-2-(4-Fluorobenzyl)-N6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)-N1-((4S,7S,10aS)-5-oxo-7-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-5-propylhexanediamide

Procedure

(2R,5S)-2-(4-Fluorobenzyl)-N6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)-N1-((4S,7S,10aS)-5-oxo-7-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-5-propylhexanediamide was synthesized as described in General Procedure H using Intermediate 76 (22 mg, 0.043 mmol) and Intermediate 77 (12 mg, 0.045 mmol) to give a white solid (14 mg, 43% yield). Anal. Calcd. for C39H50F4N4O5S m/z 762.7. found: 763.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.42-7.22 (3H, m), 7.15-7.02 (3H, m), 7.01-6.94 (2H, m), 6.86 (2H, t, J=8.5 Hz), 5.28-5.15 (2H, m), 4.99-4.83 (2H, m), 4.05-3.88 (1H, m), 3.81 (3H, s), 3.54-3.34 (1H, m), 3.28-3.09 (1H, m), 2.85-2.60 (3H, m), 2.42-2.30 (1H, m), 2.22-1.72 (12H, m), 1.71-1.20 (11H, m), 0.87 (3H, t, J=7.1 Hz).

Sources & evidence

ORD record
ord-c03af72aadbe4313827b308499cddf2a
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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