(4S,10aR)-4-aminohexahydropyrido[1,2-a][1,4]diazepine-1,5(2H,7H)-dione → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((4R,10aR)-1,5-dioxodecahydropyrido[1,2-a][1,4]diazepin-4-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529585Notes

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[C:48](=[O:49])[N:47]2[CH2:50][CH2:51][CH2:52][CH2:53][C@@H:46]2[C:45](=[O:54])[NH:44][CH2:43]1>>[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[C:48](=[O:49])[N:47]2[CH2:50][CH2:51][CH2:52][CH2:53][C@@H:46]2[C:45](=[O:54])[NH:44][CH2:43]1)=[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 68310907(4S,10aR)-4-aminohexahydropyrido[1,2-a][1,4]diazepine-1,5(2H,7H)-dione

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 86706246(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((4R,10aR)-1,5-dioxodecahydropyrido[1,2-a][1,4]diazepin-4-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-((4R,10aR)-1,5-dioxodecahydropyrido[1,2-a][1,4]diazepin-4-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 (20 mg, 0.035 mmol) and Intermediate 39 (7.0 mg, 0.035 mmol) to give a white solid (15 mg, 56% yield). Anal. Calcd. for C40H51N5O7S m/z 745.7. found: 746.5 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.92-7.70 (m, 3H), 7.29-7.02 (m, 7H), 5.67-5.52 (m, 1H), 5.09-4.91 (m, 2H), 4.36 (d, J=13.0 Hz, 1H), 3.83-3.75 (m, 1H), 3.73-3.64 (m, 1H), 3.64-3.52 (m, 4H), 3.22-2.98 (m, 2H), 2.82-2.61 (m, 4H), 2.60-2.34 (m, 8H), 2.18 (d, J=13.8 Hz, 1H), 2.09-1.88 (m, 2H), 1.86-1.73 (m, 2H), 1.71-1.15 (m, 12H).

Sources & evidence

ORD record: ord-46287cd6f3de439e92aa800f085f520d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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