N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-(2-oxopyrrolidin-1-yl)-5-phenylbenzamide → N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-2-methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxamide

HRID 1612505Notes

Reaction equation

HRID 1612505 reaction equation
C([C@H](NC(=O)C1C=C(C2C=CC=CC=2)C=C(N2CCCC2=O)C=1)[C@@H](O)C[C@H](C(=O)NCCC(C)(C)C)C)C1C=CC=CC=1.[CH3:44][O:45][C:46]1[CH:51]=[C:50]([C:52]([OH:54])=O)[CH:49]=[C:48]([N:55]2[CH2:59][CH2:58][CH2:57][C:56]2=[O:60])[N:47]=1.[CH:61]12[CH2:67][CH:64]([CH2:65][CH2:66]1)[CH2:63][CH:62]2[NH:68][C:69](=[O:84])[C@H:70]([CH3:83])[CH2:71][C@H:72]([OH:82])[C@@H:73]([NH2:81])[CH2:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1>>[CH2:74]([C@H:73]([NH:81][C:52]([C:50]1[CH:49]=[C:48]([N:55]2[CH2:59][CH2:58][CH2:57][C:56]2=[O:60])[N:47]=[C:46]([O:45][CH3:44])[CH:51]=1)=[O:54])[C@@H:72]([OH:82])[CH2:71][C@H:70]([C:69](=[O:84])[NH:68][CH:62]1[CH2:63][CH:64]2[CH2:67][CH:61]1[CH2:66][CH2:65]2)[CH3:83])[C:75]1[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=1

Participants

4

Reactant 3

HCID 10129098N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-(2-oxopyrrolidin-1-yl)-5-phenylbenzamideHCID 222530372-Methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxylic acidHCID 68889549(2R,4S,5S)-5-Amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (bicyclo[2.2.1]hept-2-yl)amide

Product 1

HCID 58583647N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-2-methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxamide

Procedure

Prepared in an analogous manner to E6, from 2-methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxylic acid (D58) and (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (bicyclo[2.2.1]hept-2-yl)amide (D29).

Sources & evidence

ORD record
ord-4d1af0873b6549128d79a19bb765d309
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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