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-hydroxy-pentyl]-3-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-benzamide

HRID 1612490Notes

Reaction equation

HRID 1612490 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.[CH:44]([C@H:47]1[CH2:51][O:50][C:49](=[O:52])[N:48]1[C:53]1[CH:54]=[C:55]([CH:59]=[CH:60][CH:61]=1)[C:56]([OH:58])=O)([CH3:46])[CH3:45].[CH:62]12[CH2:68][CH:65]([CH2:66][CH2:67]1)[CH2:64][CH:63]2[NH:69][C:70](=[O:85])[C@H:71]([CH3:84])[CH2:72][C@H:73]([OH:83])[C@@H:74]([NH2:82])[CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1>>[CH2:75]([C@H:74]([NH:82][C:56](=[O:58])[C:55]1[CH:59]=[CH:60][CH:61]=[C:53]([N:48]2[C@@H:47]([CH:44]([CH3:45])[CH3:46])[CH2:51][O:50][C:49]2=[O:52])[CH:54]=1)[C@@H:73]([OH:83])[CH2:72][C@H:71]([C:70](=[O:85])[NH:69][CH:63]1[CH2:64][CH:65]2[CH2:68][CH:62]1[CH2:67][CH2:66]2)[CH3:84])[C:76]1[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=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 68889549(2R,4S,5S)-5-Amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (bicyclo[2.2.1]hept-2-yl)amideHCID 695896963-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)benzoic acid

Product 1

HCID 58583648N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxy-pentyl]-3-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-benzamide

Procedure

Prepared in an analogous manner to E6 from 3-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)benzoic acid (D23) 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-ef793ccfb5394e01bc442bd4f0534892
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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