3-Methoxy-5-methylsulfonylbenzoic acid → N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-3-methoxy-5-methylsulfonylbenzamide

HRID 1373111Notes

Reaction equation

HRID 1373111 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][O:37][C:38]1[CH:39]=[C:40]([CH:44]=[C:45]([S:47]([CH3:50])(=[O:49])=[O:48])[CH:46]=1)[C:41]([OH:43])=O.[CH:51]12[CH2:57][CH:54]([CH2:55][CH2:56]1)[CH2:53][CH:52]2[NH:58][C:59](=[O:74])[C@H:60]([CH3:73])[CH2:61][C@H:62]([OH:72])[C@@H:63]([NH2:71])[CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>>[CH2:64]([C@H:63]([NH:71][C:41](=[O:43])[C:40]1[CH:44]=[C:45]([S:47]([CH3:50])(=[O:49])=[O:48])[CH:46]=[C:38]([O:37][CH3:36])[CH:39]=1)[C@@H:62]([OH:72])[CH2:61][C@H:60]([C:59](=[O:74])[NH:58][CH:52]1[CH2:53][CH:54]2[CH2:57][CH:51]1[CH2:56][CH2:55]2)[CH3:73])[C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1

Participants

4

Reactant 3

HCID 210741983-Methoxy-5-methylsulfonylbenzoic 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 69507949N-[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-3-methoxy-5-methylsulfonylbenzamide

Procedure

Prepared in an analogous manner to E1 from 3-methoxy-5-methylsulfonylbenzoic acid (D15) 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-f337877e5f0b4edd9c1b5f4ee34ffe04
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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