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-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzamide

HRID 1612485Notes

Reaction equation

HRID 1612485 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]([O:47][C:48]1[CH:49]=[C:50]([CH:54]=[C:55]([N:57]2[CH2:61][CH2:60][CH2:59][C:58]2=[O:62])[CH:56]=1)[C:51]([OH:53])=O)([CH3:46])[CH3:45].[CH:63]12[CH2:69][CH:66]([CH2:67][CH2:68]1)[CH2:65][CH:64]2[NH:70][C:71](=[O:86])[C@H:72]([CH3:85])[CH2:73][C@H:74]([OH:84])[C@@H:75]([NH2:83])[CH2:76][C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1>>[CH2:76]([C@H:75]([NH:83][C:51](=[O:53])[C:50]1[CH:54]=[C:55]([N:57]2[CH2:61][CH2:60][CH2:59][C:58]2=[O:62])[CH:56]=[C:48]([O:47][CH:44]([CH3:45])[CH3:46])[CH:49]=1)[C@@H:74]([OH:84])[CH2:73][C@H:72]([C:71](=[O:86])[NH:70][CH:64]1[CH2:65][CH:66]2[CH2:69][CH:63]1[CH2:68][CH2:67]2)[CH3:85])[C:77]1[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=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 222530453-Isopropoxy-5-(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 58583635N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-3-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to E6 from 3-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzoic acid (D16) 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-85689b56f1384484bf7566977c43c6d2
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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