Dimethyl L-glutamate hydrochloride → N-[5-(4-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)pentanoyl]-L-glutamic Acid

HRID 1370947Notes

Reaction equation

HRID 1370947 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:42]=[CH:41][C:25]([O:26][C:27]2[CH:40]=[CH:39][C:30]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](O)=[O:37])=[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:55])[C@H:47]([CH2:49][CH2:50][C:51]([O:53]C)=[O:52])[NH2:48]>>[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][CH2:33][CH2:34][CH2:35][C:36]([NH:48][C@H:47]([C:46]([OH:45])=[O:55])[CH2:49][CH2:50][C:51]([OH:53])=[O:52])=[O:37])=[CH:39][CH:40]=2)=[CH:41][CH:42]=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 12917568Dimethyl L-glutamate hydrochlorideHCID 185122255-(4-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)pentanoic Acid

Product 1

HCID 68857946N-[5-(4-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)pentanoyl]-L-glutamic Acid

Procedure

The product from Example 234B and L-glutamic acid dimethyl ester hydrochloride were processed as described in Example 251A and B to provide the titled compound. 1H NMR (500 MHz, DMSO-d6) δ11.60-13.04 (br.s, 2 H), 8.94 (s, 1 H), 8.06 (d, 1 H), 7.23 (m, 7 H), 7.03 (t, 1 H), 6.95 (m, 6 H), 6.82 (d, 2 H), 4.21 (m, 1 H), 4.04 (s, 2 H), 4.00 (s, 2 H), 3.93 (t, 2 H), 2.91 (s, 3 H), 2.39 (s, 3 H), 2.28 (m, 2 H), 2.19 (t, 2 H), 1.96 (m, 1 H), 1.60-1.82 (m, 5 H); MS (ESI+) m/z 718 (M+H)+.

Sources & evidence

ORD record
ord-03e5699f04664e5cb1fe859f8878bb5c
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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