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

HRID 1413009Notes

Reaction equation

HRID 1413009 reaction equation
[CH3:1][O:2][C:3](=[O:61])[NH:4][C@@H:5]([CH:58]([CH3:60])[CH3:59])[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:23]=[C:22]3[CH2:24][O:25][C:26]4[CH:57]=[C:56]5[C:29]([CH:30]=[CH:31][C:32]6[N:36]=[C:35]([C@H:37]7[N:41]([C:42](=[O:52])[C@@H:43]([NH:47][C:48]([O:50][CH3:51])=[O:49])[CH:44]([CH3:46])[CH3:45])[C@H:40]8[CH2:53][CH2:54][CH2:55][C@H:39]8[CH2:38]7)[NH:34][C:33]=65)=[CH:28][C:27]=4[C:21]3=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=[O:7].[CH3:62][O:63][C:64](N[C@@H](C(C)C)C(O)=O)=O>>[CH3:1][O:2][C:3](=[O:61])[NH:4][C@@H:5]([CH:58]1[CH2:60][CH2:64][O:63][CH2:62][CH2:59]1)[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:23]=[C:22]3[CH2:24][O:25][C:26]4[CH:57]=[C:56]5[C:29]([CH:30]=[CH:31][C:32]6[N:36]=[C:35]([C@H:37]7[N:41]([C:42](=[O:52])[C@@H:43]([NH:47][C:48]([O:50][CH3:51])=[O:49])[CH:44]([CH3:46])[CH3:45])[C@H:40]8[CH2:53][CH2:54][CH2:55][C@H:39]8[CH2:38]7)[NH:34][C:33]=65)=[CH:28][C:27]=4[C:21]3=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=[O:7]

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-44f37b67345e44a7b9654f6f35526a9b
Source dataset
uspto-grants-2014_12
Patent number
US08921341B2

Reaction notes

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