3-Methylsulfonyl-5-(2-oxopyrrolidin-1-yl)benzoic acid → N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]3-methylsulfonyl-5-(2-oxopyrrolidin-1-yl)-benzamide

HRID 1373112Notes

Reaction equation

HRID 1373112 reaction equation
C([C@H](NC(=O)C1C=CC=C(S(C)(=O)=O)C=1)[C@@H](O)C[C@H](C(=O)NCCC(C)(C)C)C)C1C=CC=CC=1.[CH3:36][S:37]([C:40]1[CH:41]=[C:42]([CH:46]=[C:47]([N:49]2[CH2:53][CH2:52][CH2:51][C:50]2=[O:54])[CH:48]=1)[C:43]([OH:45])=O)(=[O:39])=[O:38].[CH:55]12[CH2:61][CH:58]([CH2:59][CH2:60]1)[CH2:57][CH:56]2[NH:62][C:63](=[O:78])[C@H:64]([CH3:77])[CH2:65][C@H:66]([OH:76])[C@@H:67]([NH2:75])[CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1>>[CH2:68]([C@H:67]([NH:75][C:43](=[O:45])[C:42]1[CH:46]=[C:47]([N:49]2[CH2:53][CH2:52][CH2:51][C:50]2=[O:54])[CH:48]=[C:40]([S:37]([CH3:36])(=[O:38])=[O:39])[CH:41]=1)[C@@H:66]([OH:76])[CH2:65][C@H:64]([C:63](=[O:78])[NH:62][CH:56]1[CH2:57][CH:58]2[CH2:61][CH:55]1[CH2:60][CH2:59]2)[CH3:77])[C:69]1[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1

Participants

4

Reactant 3

HCID 210741993-Methylsulfonyl-5-(2-oxopyrrolidin-1-yl)benzoic acidHCID 58780868N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-methanesulfonyl-benzamideHCID 68889549(2R,4S,5S)-5-Amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (bicyclo[2.2.1]hept-2-yl)amide

Product 1

HCID 69507541N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]3-methylsulfonyl-5-(2-oxopyrrolidin-1-yl)-benzamide

Procedure

Prepared in an analogous manner to E1, from 3-methylsulfonyl-5-(2-oxopyrrolidin-1-yl)-benzoic acid (D19) and (2R,4S,5S)-5-Amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (bicyclo[2.2.1]hept-2-yl)amide (D4).

Sources & evidence

ORD record
ord-34da982ab01e408c83eaa6e90f5a97bc
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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