(Z)-3-amino-4,4-dimethyl-1-phenyl-3,4-dihydro-1H-azepin-2(7H)-one → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((S,Z)-4,4-dimethyl-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529578Notes

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][CH:42]1[C:48]([CH3:50])([CH3:49])[CH:47]=[CH:46][CH2:45][N:44]([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[C:48]([CH3:50])([CH3:49])[CH:47]=[CH:46][CH2:45][N:44]([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 68292320(Z)-3-amino-4,4-dimethyl-1-phenyl-3,4-dihydro-1H-azepin-2(7H)-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 68311199(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((S,Z)-4,4-dimethyl-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-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)-4,4-dimethyl-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-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 (10 mg, 0.018 mmol) and Intermediate 33 (4.1 mg, 0.018 mmol) to give a white solid (4.0 mg, 27% yield). Anal. Calcd. for C45H54N4O6S m/z 778.4. found: 779.4 (M+H)+; 1H NMR (500 MHz, CD3OD) δ ppm 8.00-8.08 (m, 1H), 7.31 (t, J=7.70 Hz, 2H), 7.27-7.09 (m, 11H), 6.98 (d, J=7.70 Hz, 2H), 5.77 (ddd, J=11.41, 8.11, 3.57 Hz, 1H), 5.63-5.49 (m, 2H), 5.38 (d, J=9.35 Hz, 1H), 5.04-4.97 (m, 1H), 4.96-4.90 (m, 1H), 3.75 (dd, J=17.60, 8.25 Hz, 1H), 3.59 (s, 3H), 3.03-2.88 (m, 2H), 2.84-2.65 (m, 5H), 2.62-2.53 (m, 1H), 2.34 (d, J=13.75 Hz, 1H), 2.16-2.01 (m, 1H), 1.96 (d, J=10.45 Hz, 1H), 1.89-1.79 (m, 2H), 1.76-1.47 (m, 6H), 1.41-1.30 (m, 1H), 0.89-0.80 (s, 3H), 0.54-0.46 (s, 3H).

Sources & evidence

ORD record: ord-994d339f156742419243dd17a9a34997
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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