(4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate → (4S,7S,10aS)-Methyl 4-((2R,5S)-2-(4-fluorobenzyl)-5-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamoyl)octanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529630Notes

Reaction equation

HRID 529630 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]([O:52][CH3:53])=[O:51])[N:41]2[C:40]1=[O:54]>>[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]([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]([O:52][CH3:53])=[O:51])[N:41]3[C:40]2=[O:54])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 10563170(4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylateHCID 68311019(2R,5S)-2-(4-Fluorobenzyl)-5-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamoyl)octanoic acid

Product 1

HCID 66546648(4S,7S,10aS)-Methyl 4-((2R,5S)-2-(4-fluorobenzyl)-5-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamoyl)octanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Procedure

(4S,7S,10aS)-Methyl 4-((2R,5S)-2-(4-fluorobenzyl)-5-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamoyl)octanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate was synthesized as described in General Procedure H using Intermediate 76 (10 mg, 0.020 mmol) and (4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (5.5 mg, 0.021 mmol) to give a white solid (10 mg, 70% yield). Anal. Calcd. for C40H53FN4O7S m/z 752.7. found: 753.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.53-7.43 (1H, m), 7.31 (1H, t, J=8.0 Hz), 7.28-7.18 (1H, m), 7.14-7.04 (3H, m), 7.01-6.95 (2H, m), 6.88 (2H, t, J=8.8 Hz), 5.35-5.27 (1H, m), 5.15-5.09 (1H, m), 5.04-4.95 (1H, m), 4.94-4.85 (1H, m), 4.05-3.90 (1H, m), 3.82 (3H, s), 3.69 (3H, s), 3.53-3.36 (1H, m), 3.22-3.06 (1H, m), 2.86-2.65 (3H, m), 2.45-2.32 (2H, m), 2.25-2.14 (1H, m), 2.12-1.87 (5H, m), 1.87-1.30 (14H, m), 1.30-1.20 (2H, m), 0.87 (3H, t, J=7.1 Hz).

Sources & evidence

ORD record
ord-aa18ed060f3040dcb7e471f90df4326b
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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