(4-(4-((Benzyl(2-methyl-3-((methylsulfonyl)amino)phenyl)amino)methyl)phenoxy)phenoxy)acetic acid → N~2~-[(4-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)acetyl]-L-asparagine

HRID 1370956Notes

Reaction equation

HRID 1370956 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:39]=[CH:38][C:25]([O:26][C:27]2[CH:37]=[CH:36][C:30]([O:31][CH2:32][C:33](O)=[O:34])=[CH:29][CH:28]=2)=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O:45][C:46](=[O:53])[C@H:47]([CH2:49][C:50](=[O:52])[NH2:51])[NH2:48])(C)(C)C>>[CH2:1]([N:8]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][C:27]2[CH:28]=[CH:29][C:30]([O:31][CH2:32][C:33]([NH:48][C@H:47]([C:46]([OH:45])=[O:53])[CH2:49][C:50](=[O:52])[NH2:51])=[O:34])=[CH:36][CH:37]=2)=[CH:38][CH:39]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[C:10]=1[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 11410199(4-(4-((Benzyl(2-methyl-3-((methylsulfonyl)amino)phenyl)amino)methyl)phenoxy)phenoxy)acetic acidHCID 16218498tert-Butyl L-asparaginate--hydrogen chloride (1/1)

Product 1

HCID 21130136N~2~-[(4-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)acetyl]-L-asparagine

Procedure

The product from Example 95C and L-aspargine tert-butyl ester hydrochloride were processed as described in Example 251A and 258B to provide the titled compound. 1H NMR (500 MHz, DMSO-d6) δ12.18-13.09 (br.s, 1 H), 8.94 (s, 1 H), 8.28 (d, 1 H), 7.39 (s, 1 H), 7.23 (m, 7 H), 7.03 (t, 1 H), 6.94 (m, 6 H), 6.91 (s, 1 H), 6.84 (d, 2 H), 4.60 (dd, 1 H), 4.49 (s, 2 H), 4.05 (s, 2 H), 4.00 (s, 2 H), 2.91 (s, 3 H), 2.60 (d2 H), 2.39 (s, 3 H); MS ((ESI+) m/z 661 (M+H)+.

Sources & evidence

ORD record
ord-d47e4d05bf184ab490304c2dd278b613
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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