N-Methoxycarbonyl-2-phenylglycine → [1-(2-{5-[6-(4-{2-[4-Cyano-1-(2-methoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:60])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][C:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:31]4[CH:36]=[CH:35][C:34]([C:37]5[NH:38][C:39]([CH:42]6[CH2:46][CH:45]([C:47]#[N:48])[CH2:44][N:43]6[C:49](=[O:59])[CH:50]([NH:54][C:55]([O:57][CH3:58])=[O:56])[CH:51]([CH3:53])[CH3:52])=[N:40][CH:41]=5)=[CH:33][CH:32]=4)[CH:27]=3)[CH:22]=2)=[CH:19][N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].C(N1CC[CH2:68][C@H:64]1[C:65](O)=O)#N.COC(NC(C1C=CC=CC=1)C(O)=O)=O>>[CH3:1][O:2][C:3](=[O:60])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][C:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:31]4[CH:36]=[CH:35][C:34]([C:37]5[NH:38][C:39]([CH:42]6[CH2:46][CH:45]([C:47]#[N:48])[CH2:44][N:43]6[C:49](=[O:59])[CH:50]([NH:54][C:55]([O:57][CH3:58])=[O:56])[C:51]6[CH:53]=[CH:68][CH:64]=[CH:65][CH:52]=6)=[N:40][CH:41]=5)=[CH:33][CH:32]=4)[CH:27]=3)[CH:22]=2)=[CH:19][N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7]Participants
4
Reactant 3
Product 1
Procedure
Synthesized similar to [1-(2-{5-[6-(4-{2-[4-Cyano-1-(2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester, reverting the order of Suzuki coupling and reaction introduction of the amino acid moiety on the cyano proline using methoxycarbonylamino-phenyl-acetic acid.
Sources & evidence
- ORD record
- ord-852e20e4e872406d9235f5d81005fa8d
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156823B2
Reaction notes
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