(S,Z)-3-amino-1-phenyl-1,4,5,8-tetrahydroazocin-2(3H)-one → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S,Z)-2-oxo-1-phenyl-1,2,3,4,5,8-hexahydroazocin-3-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529611Notes

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][S:22][C@H:21]2[CH2:25][CH2:26][CH2:27][C@@H:28]([C:29]([O:31][CH3:32])=[O:30])[N:20]2[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[CH2:49][CH2:48][CH:47]=[CH:46][CH2:45][N:44]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:43]1=[O:56]>>[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](=[O:10])[NH:41][C@H:42]1[CH2:49][CH2:48][CH:47]=[CH:46][CH2:45][N:44]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:43]1=[O:56])[C:15]([NH:17][C@H:18]1[CH2:24][CH2:23][S:22][C@H:21]2[CH2:25][CH2:26][CH2:27][C@@H:28]([C:29]([O:31][CH3:32])=[O:30])[N:20]2[C:19]1=[O:33])=[O:16])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Reactant 2

HCID 68292461(S,Z)-3-amino-1-phenyl-1,4,5,8-tetrahydroazocin-2(3H)-one

HCID 68311179(2R,5R)-2,5-Dibenzyl-6-((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-6-oxohexanoic acid

Product 1

HCID 68311204(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S,Z)-2-oxo-1-phenyl-1,2,3,4,5,8-hexahydroazocin-3-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Procedure

(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S,Z)-2-oxo-1-phenyl-1,2,3,4,5,8-hexahydroazocin-3-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate was synthesized as described in General Procedure H using Intermediate 23 (11 mg, 0.019 mmol) and Intermediate 63 (5.6 mg, 0.022 mmol) to give a white solid (3.5 mg, 25% yield). Anal. Calcd. for C44H52N4O6S m/z 764.4. found: 765.4 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.40-7.09 (16H, m), 7.00 (1H, d, J=7.1 Hz), 5.98-5.87 (1H, m), 5.60 (1H, d, J=11.5 Hz), 5.34 (1H, t, J=4.7 Hz), 5.11-5.05 (1H, m), 5.04-4.84 (3H, m), 4.06-3.97 (1H, m), 3.66 (3H, s), 3.08-2.99 (1H, m), 2.87-2.70 (5H, m), 2.49-2.33 (4H, m), 2.13-1.96 (3H, m), 1.88-1.73 (3H, m), 1.71-1.51 (7H, m), 1.38-1.28 (1H, m).

Sources & evidence

ORD record: ord-84a33061d537452ca3477f7e6ff70eb1
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

Loading…