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]-3-(2-oxooxazolidin-3-yl)benzamide

HRID 1612488Notes

Reaction equation

HRID 1612488 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.[O:44]=[C:45]1[N:49]([C:50]2[CH:51]=[C:52]([CH:56]=[CH:57][CH:58]=2)[C:53]([OH:55])=O)[CH2:48][CH2:47][O:46]1.[CH:59]12[CH2:65][CH:62]([CH2:63][CH2:64]1)[CH2:61][CH:60]2[NH:66][C:67](=[O:82])[C@H:68]([CH3:81])[CH2:69][C@H:70]([OH:80])[C@@H:71]([NH2:79])[CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1>>[CH2:72]([C@H:71]([NH:79][C:53](=[O:55])[C:52]1[CH:56]=[CH:57][CH:58]=[C:50]([N:49]2[CH2:48][CH2:47][O:46][C:45]2=[O:44])[CH:51]=1)[C@@H:70]([OH:80])[CH2:69][C@H:68]([C:67](=[O:82])[NH:66][CH:60]1[CH2:61][CH:62]2[CH2:65][CH:59]1[CH2:64][CH2:63]2)[CH3:81])[C:73]1[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=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 222530423-(2-Oxo-1,3-oxazolidin-3-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 58583646N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-3-(2-oxooxazolidin-3-yl)benzamide

Procedure

Prepared in an analogous manner to E6, from 3-(2-oxooxazolidin-3-yl)benzoic acid (D19) 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-41bb761810b8497a9f8eacff0afa0199
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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