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-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide

HRID 1612493Notes

Reaction equation

HRID 1612493 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][C:51]([N:60]2[CH2:64][CH2:63][CH2:62][C:61]2=[O:65])=[CH:50][C:46]=1[C:47]([OH:49])=O.[CH:66]12[CH2:72][CH:69]([CH2:70][CH2:71]1)[CH2:68][CH:67]2[NH:73][C:74](=[O:89])[C@H:75]([CH3:88])[CH2:76][C@H:77]([OH:87])[C@@H:78]([NH2:86])[CH2:79][C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1>>[CH2:79]([C@H:78]([NH:86][C:47](=[O:49])[C:46]1[CH:50]=[C:51]([N:60]2[CH2:64][CH2:63][CH2:62][C:61]2=[O:65])[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:77]([OH:87])[CH2:76][C@H:75]([C:74](=[O:89])[NH:73][CH:67]1[CH2:68][CH:69]2[CH2:72][CH:66]1[CH2:71][CH2:70]2)[CH3:88])[C:80]1[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=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 222530082-Fluoro-3,5-bis-(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 23594067N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-2-fluoro-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to E6 from 2-fluoro-3,5-bis-(2-oxopyrrolidin-1-yl)benzoic acid (D40) 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-103ee08a24a64790a5dac0c697399a48
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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