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

HRID 529577Notes

Reaction equation

HRID 529577 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.Cl.[NH2:42][C@H:43]1[CH2:48][CH2:47][CH2:46][N:45]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:44]1=[O:55]>>[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:42][C@H:43]1[CH2:48][CH2:47][CH2:46][N:45]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:44]1=[O:55])[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

3

Reactant 2

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 acidHCID 86706241(S)-3-Amino-1-phenylpiperidin-2-one mono hydrochloride

Product 1

HCID 68310949(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S)-2-oxo-1-phenylpiperidin-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-phenylpiperidin-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 (10 mg, 0.018 mmol) and Intermediate 32 (3.4 mg, 0.018 mmol) to give a white solid (5.0 mg, 36% yield). Anal. Calcd. for C42H50N4O6S m/z 738.4. found: 739.4 (M+H)+; 1H NMR (500 MHz, CD3OD) δ ppm 7.46-7.35 (m, 2H), 7.32-7.25 (m, 3H), 7.23-7.08 (m, 10H), 5.49 (dd, J=6.32, 3.02 Hz, 1H), 5.08-5.02 (m, 1H), 4.98-4.91 (m, 1H), 4.17 (dd, J=11.00, 6.05 Hz, 1H), 3.97 (s, 1H), 3.73 (d, J=7.15 Hz, 1H), 3.64 (s, 3H), 3.09 (s, 1H), 2.89-2.76 (m, 2H), 2.76-2.65 (m, 3H), 2.65-2.51 (m, 2H), 2.31 (br. s., 1H), 2.11-1.91 (m, 5H), 1.90-1.80 (m, 1H), 1.77-1.55 (m, 7H), 1.57-1.46 (m, 2H).

Sources & evidence

ORD record
ord-d70f8816785043ab9589b66798052f7b
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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