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

HRID 1612481Notes

Reaction equation

HRID 1612481 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[CH2:49][CH2:48][CH2:47][N:46]1[C:50]1[CH:51]=[C:52]([CH:56]=[C:57]([N:59]2[CH2:63][CH2:62][CH2:61][C:60]2=[O:64])[CH:58]=1)[C:53](O)=[O:54].[CH:65]12[CH2:71][CH:68]([CH2:69][CH2:70]1)[CH2:67][CH:66]2[NH:72][C:73](=[O:88])[C@H:74]([CH3:87])[CH2:75][C@H:76]([OH:86])[C@@H:77]([NH2:85])[CH2:78][C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1>>[CH2:78]([C@H:77]([NH:85][C:53](=[O:54])[C:52]1[CH:51]=[C:50]([N:46]2[CH2:47][CH2:48][CH2:49][C:45]2=[O:44])[CH:58]=[C:57]([N:59]2[CH2:63][CH2:62][CH2:61][C:60]2=[O:64])[CH:56]=1)[C@@H:76]([OH:86])[CH2:75][C@H:74]([C:73](=[O:88])[NH:72][CH:66]1[CH2:67][CH:68]2[CH2:71][CH:65]1[CH2:70][CH2:69]2)[CH3:87])[C:79]1[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=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 111620233,5-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 23594068N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-3,5-bis(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to E6, from 3,5-bis-(2-oxopyrrolidin-1-yl)benzoic acid (D8) 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-1b4451982f344f4a8193b4fba9c92c35
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

Loading…