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

HRID 529593Notes

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][CH:48]=[CH:47][CH2:46][CH2:45][N:44]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=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[CH2:49][CH:48]=[CH:47][CH2:46][CH2:45][N:44]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:43]1=[O:57])=[O:10])[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 68292242(S,Z)-3-amino-1-benzyl-3,4,7,8-tetrahydroazocin-2(1H)-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 66547009(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((S,Z)-1-benzyl-2-oxo-1,2,3,4,7,8-hexahydroazocin-3-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Procedure

(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((S,Z)-1-benzyl-2-oxo-1,2,3,4,7,8-hexahydroazocin-3-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate was synthesized as described in General Procedure H using Intermediate 23 (8.0 mg, 0.014 mmol) and Intermediate 44 (6.5 mg, 0.028 mmol) to give a white solid (6.8 mg, 61% yield). Anal. Calcd. for C45H54N4O6S m/z 778.7. found: 779.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.40-7.05 (m, 17H), 5.48-5.26 (m, 4H), 5.18-5.06 (m, 1H), 5.05-4.93 (m, 3H), 4.84 (d, J=14.8 Hz, 1H), 4.17 (d, J=14.8 Hz, 1H), 3.92-3.75 (m, 1H), 3.67 (s, 3H), 3.14 (dt, J=14.3, 8.7 Hz, 2H), 2.87-2.66 (m, 5H), 2.61-2.32 (m, 6H), 2.25 (dt, J=16.4, 8.0 Hz, 1H), 2.06-1.97 (m, 2H), 1.86-1.44 (m, 7H).

Sources & evidence

ORD record: ord-e0f32c70287d4bbbb1837854bf71afef
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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