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-fluoro-3-(2-oxopyrrolidin-1-yl)-benzamide

HRID 1612492Notes

Reaction equation

HRID 1612492 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.[F:44][C:45]1[C:53]([N:54]2[CH2:58][CH2:57][CH2:56][C:55]2=[O:59])=[CH:52][CH:51]=[CH:50][C:46]=1[C:47]([OH:49])=O.[CH:60]12[CH2:66][CH:63]([CH2:64][CH2:65]1)[CH2:62][CH:61]2[NH:67][C:68](=[O:83])[C@H:69]([CH3:82])[CH2:70][C@H:71]([OH:81])[C@@H:72]([NH2:80])[CH2:73][C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1>>[CH2:73]([C@H:72]([NH:80][C:47](=[O:49])[C:46]1[CH:50]=[CH:51][CH:52]=[C:53]([N:54]2[CH2:58][CH2:57][CH2:56][C:55]2=[O:59])[C:45]=1[F:44])[C@@H:71]([OH:81])[CH2:70][C@H:69]([C:68](=[O:83])[NH:67][CH:61]1[CH2:62][CH:63]2[CH2:66][CH:60]1[CH2:65][CH2:64]2)[CH3:82])[C:74]1[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=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 222529812-Fluoro-3-(2-oxopyrrolidin-1-yl)benzoic 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 58583636N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-2-fluoro-3-(2-oxopyrrolidin-1-yl)-benzamide

Procedure

Prepared in an analogous manner to E6 from 2-fluoro-3-(2-oxopyrrolidin-1-yl)benzoic acid (D27) 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-4564ef8c918c425288481af7029bf631
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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