(S)-2-({(S)-6-(2-acetylamino-4-methyl-thiazole-5-sulfonyl)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2-oxo-2,3,5,6,7,8-hexahydro-1H-4-oxa-1,6-diaza-anthracene-7-carbonyl}-amino)-3-(4'-cyano-biphenyl-4-yl)-propionic acid methyl ester → HCID 86636875, compound

HRID 2273450Notes

Reaction equation

C[O:2][C:3](=[O:67])[C@@H:4]([NH:20][C:21]([CH:23]1[CH2:36][C:35]2[CH:34]=[C:33]3[C:28]([O:29][C@@H:30]([C:38]4[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]5[CH:51]=[CH:50][C:49]([Cl:52])=[C:48]([Cl:53])[CH:47]=5)=[CH:40][CH:39]=4)[C:31](=[O:37])[NH:32]3)=[CH:27][C:26]=2[CH2:25][N:24]1[S:54]([C:57]1[S:61][C:60]([NH:62]C(=O)C)=[N:59][C:58]=1[CH3:66])(=[O:56])=[O:55])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.COC(=O)[C@@H](NC(C1CC2C=C3C(O[C@@H](C4C=CC(OCC5C=CC(Cl)=C(Cl)C=5)=CC=4)C(=O)N3)=CC=2CN1S(C1SC(N)=NC=1C)(=O)=O)=O)CC1C=CC(C2C=CC(C#N)=CC=2)=CC=1>>[NH2:62][C:60]1[S:61][C:57]([S:54]([N:24]2[CH:23]([C:21]([NH:20][C@@H:4]([CH2:5][C:6]3[CH:7]=[CH:8][C:9]([C:12]4[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[CH:16][CH:17]=4)=[CH:10][CH:11]=3)[C:3]([OH:67])=[O:2])=[O:22])[CH2:36][C:35]3[CH:34]=[C:33]4[C:28]([O:29][C@@H:30]([C:38]5[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]6[CH:51]=[CH:50][C:49]([Cl:52])=[C:48]([Cl:53])[CH:47]=6)=[CH:40][CH:39]=5)[C:31](=[O:37])[NH:32]4)=[CH:27][C:26]=3[CH2:25]2)(=[O:56])=[O:55])=[C:58]([CH3:66])[N:59]=1

Participants

Reactant 2

HCID 86636869(S)-2-({(S)-6-(2-acetylamino-4-methyl-thiazole-5-sulfonyl)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2-oxo-2,3,5,6,7,8-hexahydro-1H-4-oxa-1,6-diaza-anthracene-7-carbonyl}-amino)-3-(4'-cyano-biphenyl-4-yl)-propionic acid methyl ester

HCID 86636876HCID 86636876, compound

Product 1

HCID 86636875HCID 86636875, compound

Procedure

(S)-2-({(S)-6-(2-Acetylamino-4-methyl-thiazole-5-sulfonyl)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2-oxo-2,3,5,6,7,8-hexahydro-1H-4-oxa-1,6-diaza-anthracene-7-carbonyl}-amino)-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester (more polar diastereomer, 100 mg) was converted to (S)-2-({(S)-6-(2-amino-4-methyl-thiazole-5-sulfonyl)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2-oxo-2,3,5,6,7,8-hexahydro-1H-4-oxa-1,6-diaza-anthracene-7-carbonyl}-amino)-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester (LC-MS m/z 941) following the general procedure P. This ester on hydrolysis using general procedure B furnished title compound (more polar diastereomer, 70 mg). LC-MS (m/z): 923.

Sources & evidence

ORD record: ord-88f02e5753ba4bb9a8947ec566cfc47e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120813B2

Reaction notes

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