(2R,5R)-2,5-dibenzyl-6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylamino)-6-oxohexanoic acid → (2R,5R)-2,5-Dibenzyl-N1-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)-N6-((4S,7S,10aS)-5-oxo-7-vinyloctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

HRID 529624Notes

Reaction equation

HRID 529624 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]([CH:53]=[CH2:54])[N:44]2[C:43]1=[O:55]>>[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]([CH:53]=[CH2:54])[N:44]2[C:43]1=[O:55])=[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 68310532(2R,5R)-2,5-dibenzyl-6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylamino)-6-oxohexanoic acidHCID 86706234(4S,7S,10aS)-4-Amino-7-vinylhexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

Product 1

HCID 68311191(2R,5R)-2,5-Dibenzyl-N1-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)-N6-((4S,7S,10aS)-5-oxo-7-vinyloctahydro-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,7S,10aS)-5-oxo-7-vinyloctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide was synthesized as described in General Procedure H using Intermediate 70 (36 mg, 0.067 mmol) and Intermediate 73 (23 mg, 0.067 mmol) to give a white solid (30 mg, 59% yield). Anal. Calcd. for C44H54N4O5S m/z 750.7. found: 751.5 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.29-7.07 (m, 11H), 7.07-6.89 (m, 3H), 6.36-6.18 (m, 1H), 5.33 (s, 1H), 5.23 (d, J=17.1 Hz, 1H), 5.12 (d, J=10.3 Hz, 1H), 5.06-4.90 (m, 2H), 4.84-4.70 (m, 1H), 4.02-3.84 (m, 1H), 3.79 (s, 3H), 3.47-3.29 (m, 1H), 3.04-2.89 (m, 1H), 2.89-2.75 (m, 2H), 2.75-2.64 (m, 1H), 2.61-2.47 (m, 1H), 2.46-2.23 (m, 8H), 2.10-1.55 (m, 11H), 1.54-1.42 (m, 2H), 1.39-1.15 (m, 2H).

Sources & evidence

ORD record
ord-7a85605543f54742ab0b5eb044aa03f6
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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