2-Piperidone → N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxy-pentyl]-3-methoxy-5-(2-oxopiperidin-1-yl)benzamide

HRID 1612486Notes

Reaction equation

HRID 1612486 reaction equation
C([C@H](NC(=O)C1C=CC(F)=[C:27]([N:32]2[CH2:36][CH2:35][CH2:34][C:33]2=[O:37])C=1)[C@@H](O)C[C@H](C(=O)NCCC(C)(C)C)C)C1C=CC=CC=1.[CH2:39]([C@H:46]([NH:61][C:62](=[O:72])[C:63]1[CH:68]=[C:67]([O:69][CH3:70])[CH:66]=[C:65](Br)[CH:64]=1)[C@@H:47]([OH:60])[CH2:48][C@H:49]([C:51](=[O:59])[NH:52][CH2:53][CH2:54][C:55]([CH3:58])(C)[CH3:56])[CH3:50])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[C:73]1(=O)NCCC[CH2:74]1>>[CH2:39]([C@H:46]([NH:61][C:62](=[O:72])[C:63]1[CH:64]=[C:65]([N:32]2[CH2:27][CH2:36][CH2:35][CH2:34][C:33]2=[O:37])[CH:66]=[C:67]([O:69][CH3:70])[CH:68]=1)[C@@H:47]([OH:60])[CH2:48][C@H:49]([C:51](=[O:59])[NH:52][CH:53]1[CH2:54][CH:55]2[CH2:56][CH:73]1[CH2:74][CH2:58]2)[CH3:50])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

4

Reactant 3

HCID 126652-PiperidoneHCID 10152661N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-4-fluoro-3-(2-oxopyrrolidin-1-yl)-benzamideHCID 69589673N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-bromo-5-methoxybenzamide

Product 1

HCID 58583652N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxy-pentyl]-3-methoxy-5-(2-oxopiperidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to E1, from N-[(1S,2S,4R)-1-benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-bromo-5-methoxybenzamide (D17) and δ-valerolactam.

Sources & evidence

ORD record
ord-73a513967796497ba547dad5a18bd15e
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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