(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acid → HCID 86708715, compound

HRID 1751370Notes

Reaction equation

HRID 1751370 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:61]([CH3:63])[CH3:62])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:15][C:16]([C:19]2[CH:20]=[CH:21][C:22]3[C:31]4[C:26](=[C:27]5[CH:35]=[CH:34][C:33]([C:36]6[NH:40][C:39]([C@@H:41]7[CH2:45][CH2:44][CH2:43][N:42]7[C:46](=[O:59])[C@H:47]([NH:54][C:55](=[O:58])[O:56][CH3:57])[C:48]7C=CC=C[CH:49]=7)=[N:38][CH:37]=6)=[CH:32][C:28]5=[CH:29][CH:30]=4)[O:25][CH2:24][C:23]=3[CH:60]=2)=[CH:17][N:18]=1)=[O:8])=[O:4].[CH3:64][O:65][C:66](N[C@@H](C(C)C)C(O)=O)=O.[CH3:76][O:77]C(N[C@H](C1C=CC=CC=1)C(O)=O)=O>>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:61]1[CH2:63][CH2:66][O:65][CH2:64][CH2:62]1)[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:15][C:16]([C:19]2[CH:20]=[CH:21][C:22]3[C:31]4[C:26](=[C:27]5[CH:35]=[CH:34][C:33]([C:36]6[NH:40][C:39]([C@@H:41]7[CH2:45][CH2:44][CH2:43][N:42]7[C:46](=[O:59])[C@@H:47]([NH:54][C:55](=[O:58])[O:56][CH3:57])[C@H:48]([O:77][CH3:76])[CH3:49])=[N:38][CH:37]=6)=[CH:32][C:28]5=[CH:29][CH:30]=4)[O:25][CH2:24][C:23]=3[CH:60]=2)=[CH:17][N:18]=1)=[O:8])=[O:4]

Participants

4

Reactant 3

HCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acidHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 67681424methyl (R)-2-((S)-2-(5-(8-(2-((S)-1-((S)-2-methoxycarbonylamino-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)-6H-dibenzo[c,h]chromen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate

Product 1

HCID 86708715HCID 86708715, compound

Procedure

This compound was made in an analogous manner to methyl (R)-2-((S)-2-(5-(8-(2-((S)-1-((S)-2-methoxycarbonylamino-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)-6H-dibenzo[c,h]chromen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate, substituting (S)-2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid for (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid in the first amide coupling, and substituting (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid for (R)-2-(methoxycarbonylamino)-2-phenylacetic acid in the second amide coupling. LCMS-ESI+: calculated for C47H54N8O9: 874.98; observed [M+1]+: 876.01.

Sources & evidence

ORD record
ord-2a072c8ec3db4aebab702c0efb4ce5f7
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

Loading…