(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid → HCID 178502492, compound

HRID 1509737Notes

Reaction equation

HRID 1509737 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:59]([CH3:61])[CH3:60])[C:7]([N:9]1[C@H:13]([C:14]2[NH:18][C:17]3[C:19]4[C:24]([CH:25]=[CH:26][C:16]=3[N:15]=2)=[CH:23][C:22]2[C:27]3[C:32]([CH2:33][O:34][C:21]=2[CH:20]=4)=[CH:31][C:30]([C:35]2[NH:39][C:38]([CH:40]4[CH2:44][CH2:43][CH2:42][N:41]4[C:45](=[O:55])[C@@H:46]([NH:50][C:51](=[O:54])[O:52][CH3:53])[CH:47]([CH3:49])[CH3:48])=[N:37][CH:36]=2)=[CH:29][CH:28]=3)[CH2:12][C@@H:11]2[CH2:56][CH2:57][CH2:58][C@H:10]12)=[O:8])=[O:4].[CH3:62][O:63][C:64](N[C@@H](C(C)C)C(O)=O)=O>>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:59]([CH3:61])[CH3:60])[C:7]([N:9]1[C@H:13]([C:14]2[NH:18][C:17]3[C:19]4[C:24]([CH:25]=[CH:26][C:16]=3[N:15]=2)=[CH:23][C:22]2[C:27]3[C:32]([CH2:33][O:34][C:21]=2[CH:20]=4)=[CH:31][C:30]([C:35]2[NH:39][C:38]([CH:40]4[CH2:44][CH2:43][CH2:42][N:41]4[C:45](=[O:55])[C@@H:46]([NH:50][C:51](=[O:54])[O:52][CH3:53])[CH:47]4[CH2:49][CH2:64][O:63][CH2:62][CH2:48]4)=[N:37][CH:36]=2)=[CH:29][CH:28]=3)[CH2:12][C@@H:11]2[CH2:56][CH2:57][CH2:58][C@H:10]12)=[O:8])=[O:4]

Participants

3

Reactant 2

HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 178502302HCID 178502302, compound

Product 1

HCID 178502492HCID 178502492, compoundYield 56%

Procedure

This compound was made in an analogous manner to methyl {(2S)-1-[2-(5-{2-[(2S,3aS,6aS)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}octahydrocyclopenta[b]pyrrol-2-yl]-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate, substituting (S)-2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid for (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid to give methyl [(1S)-2-[2-(5-{2-[(2S,3aS,6aS)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}octahydrocyclopenta[b]pyrrol-2-yl]-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)pyrrolidin-1-yl]-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethyl]carbamate (0.039 g, 56%). MS (ESI) m/z 874.34 [M+H]+. 1H NMR (400 MHz, cd3od) δ 8.58 (s, 2H), 8.26-8.08 (m, 2H), 7.96-7.75 (m, 4H), 7.65-7.54 (m, 5H), 5.36-5.11 (m, 4H), 4.34-4.04 (m, 4H), 3.97-3.79 (m, 4H), 3.65 (s, 4H), 3.53-3.44 (m, 2H), 2.68-2.47 (m, 4H), 2.32-2.02 (m, 7H), 1.95-1.82 (m, 3H), 1.77-1.54 (m, 4H), 1.49-1.24 (m, 5H), 1.10-0.99 (m, 3H), 0.92-0.85 (m, 4H).

Sources & evidence

ORD record
ord-a80c97c1b40c48328257f790f59a1634
Source dataset
uspto-grants-2015_12
Patent number
US09221833B2

Reaction notes

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