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-((R)-4-benzyl-2-oxooxazolidin-3-yl)benzamide

HRID 1612489Notes

Reaction equation

HRID 1612489 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.[CH2:44]([C@@H:51]1[CH2:55][O:54][C:53](=[O:56])[N:52]1[C:57]1[CH:58]=[C:59]([CH:63]=[CH:64][CH:65]=1)[C:60](O)=[O:61])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[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:60](=[O:61])[C:59]1[CH:63]=[CH:64][CH:65]=[C:57]([N:52]2[C@H:51]([CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH2:55][O:54][C:53]2=[O:56])[CH:58]=1)[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:85]=[CH:84][CH:83]=[CH:82][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 695897623-((R)-4-benzyl-2-oxooxazolidin-3-yl)benzoic acid

Product 1

HCID 58583633N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)benzamide

Procedure

Prepared in an analogous manner to E6 from 3-((R)-4-benzyl-2-oxooxazolidin-3-yl)benzoic acid (D21) 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-0d5d445b103b4f239167fca712e61e06
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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