(S)-3-amino-1-(pyridin-3-ylmethyl)azepan-2-one → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S)-2-oxo-1-(pyridin-3-ylmethyl)azepan-3-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529589Notes

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]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:41][C@H:42]1[CH2:48][CH2:47][CH2:46][CH2:45][N:44]([CH2:49][C:50]2[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=2)[C:43]1=[O:56]>>[CH2:34]([C@@H:14]([CH2:13][CH2:12][C@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9](=[O:11])[NH:41][C@H:42]1[CH2:48][CH2:47][CH2:46][CH2:45][N:44]([CH2:49][C:50]2[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=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:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

Reactant 2

HCID 68291953(S)-3-amino-1-(pyridin-3-ylmethyl)azepan-2-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 68309862(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S)-2-oxo-1-(pyridin-3-ylmethyl)azepan-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)-2-oxo-1-(pyridin-3-ylmethyl)azepan-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 (7.0 mg, 0.012 mmol) and Intermediate 41 (4.4 mg, 0.020 mmol) to give a white solid (4.5 mg, 47% yield). Anal. Calcd. for C43H53N5O6S m/z 767.7. found: 768.7 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 8.79 (br. s., 1H), 8.69 (d, J=4.95 Hz, 1H), 8.11 (d, J=7.70 Hz, 1H), 7.70 (dd, J=7.70, 5.50 Hz, 1H), 7.22 (t, J=7.42 Hz, 4H), 7.19-7.10 (m, 6H), 6.98 (d, J=6.60 Hz, 1H), 6.79 (d, J=6.60 Hz, 1H), 5.35-5.28 (m, 1H), 5.15-5.08 (m, 1H), 4.98 (br. s., 1H), 4.88 (d, J=15.40 Hz, 1H), 4.68-4.57 (m, 1H), 4.44 (d, J=15.40 Hz, 1H), 3.67 (s, 3H), 3.60 (dd, J=15.12, 11.82 Hz, 1H), 3.29-3.10 (m, 2H), 2.84-2.77 (m, 3H), 2.77-2.67 (m, 2H), 2.04-1.97 (m, 2H), 1.90-1.48 (m, 13H), 1.26 (t, J=7.15 Hz, 2H), 1.13 (d, J=13.20 Hz, 2H).

Sources & evidence

ORD record: ord-04489c9d4461439aac6ebaee48bc2c2f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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