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

HRID 529612Notes

Reaction equation

HRID 529612 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][CH2:48][CH2:47][CH2:46][CH2:45][N:44]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:43]1=[O:56]>>[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:41][C@H:42]1[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][N:44]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=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:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 68292040(S)-3-Amino-1-phenylazocan-2-oneHCID 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 68311203(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S)-2-oxo-1-phenylazocan-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-phenylazocan-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 (11 mg, 0.019 mmol) and Intermediate 64 (5.7 mg, 0.022 mmol) to give a white solid (6.6 mg, 46% yield). Anal. Calcd. for C44H54N4O6S m/z 766.5. found: 767.5 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.41-7.34 (2H, m), 7.31-7.03 (14H, m), 6.84 (1H, d, J=7.7 Hz), 5.32 (1H, t, J=4.7 Hz), 5.14-5.09 (1H, m), 5.06-4.98 (1H, m), 4.97-4.90 (1H, m), 4.19 (1H, t, J=14.0 Hz), 3.67 (3H, s), 3.53 (1H, d, J=14.3 Hz), 3.07 (1H, ddd, J=14.2, 11.1, 2.7 Hz), 2.87-2.67 (5H, m), 2.43-2.26 (3H, m), 2.04-1.95 (2H, m), 1.82-1.45 (16H, m), 1.34-1.24 (1H, m).

Sources & evidence

ORD record
ord-bbe15ebded5d44328a9d03cf2e3f64a3
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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