N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethyl-butylcarbamoyl)-2-hydroxypenty]-3,5-bis-(2-oxo-pyrrolidin-1-yl)benzamide → N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxyhept-6-ynyl]-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide

HRID 1612482Notes

Reaction equation

HRID 1612482 reaction equation
C([C@H](N[C:24](=[O:43])[C:25]1[CH:30]=[C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])[CH:28]=[C:27]([N:37]2[CH2:41][CH2:40][CH2:39][C:38]2=[O:42])[CH:26]=1)[C@@H](O)C[C@H](C(=O)NCCC(C)(C)C)C)C1C=CC=CC=1.O=C1CCCN1C1C=C(C=C(N2CCCC2=O)C=1)C(O)=O.[CH:65]12[CH2:71][CH:68]([CH2:69][CH2:70]1)[CH2:67][CH:66]2[NH:72][C:73](=[O:90])[C@H:74]([CH2:87][C:88]#[CH:89])[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:24](=[O:43])[C:25]1[CH:30]=[C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])[CH:28]=[C:27]([N:37]2[CH2:41][CH2:40][CH2:39][C:38]2=[O:42])[CH:26]=1)[C@@H:76]([OH:86])[CH2:75][C@H:74]([C:73](=[O:90])[NH:72][CH:66]1[CH2:67][CH:68]2[CH2:71][CH:65]1[CH2:70][CH2:69]2)[CH2:87][C:88]#[CH:89])[C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1

Participants

4

Reactant 3

HCID 10196800N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethyl-butylcarbamoyl)-2-hydroxypenty]-3,5-bis-(2-oxo-pyrrolidin-1-yl)benzamideHCID 111620233,5-bis(2-oxopyrrolidin-1-yl)benzoic AcidHCID 86759925(2R,4S,5S)-5-Amino-4-hydroxy-6-phenyl-2-prop-2-ynylhexanoic acid bicyclo[2.2.1]hept-2-ylamide

Product 1

HCID 23594066N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxyhept-6-ynyl]-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to E5 from 3,5-bis-(2-oxopyrrolidin-1-yl)benzoic acid (D8) and (2R,4S,5S)-5-amino-4-hydroxy-6-phenyl-2-prop-2-ynylhexanoic acid bicyclo[2.2.1]hept-2-ylamide (D36).

Sources & evidence

ORD record
ord-f71b724fec6043068251d61167bb3168
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

Loading…