Leucine methyl ester hydrochloride → N-[4-(3-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)butanoyl]-L-leucine

HRID 1370966Notes

Reaction equation

HRID 1370966 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:41]=[CH:40][C:25]([O:26][C:27]2[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=2)[O:30][CH2:31][CH2:32][CH2:33][C:34](O)=[O:35])=[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:44][C:45](=[O:52])[C@H:46]([CH2:48][CH:49]([CH3:51])[CH3:50])[NH2:47]>>[CH2:1]([N:8]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][C:27]2[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=2)[O:30][CH2:31][CH2:32][CH2:33][C:34]([NH:47][C@H:46]([C:45]([OH:44])=[O:52])[CH2:48][CH:49]([CH3:51])[CH3:50])=[O:35])=[CH:40][CH:41]=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 2723695Leucine methyl ester hydrochlorideHCID 185121684-(3-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)butanoic Acid

Product 1

HCID 68855209N-[4-(3-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)butanoyl]-L-leucine

Procedure

The product from Example 116B (57 mg, 0.10 mmole) and L-leucine methyl ester hydrochloride (36 mg, 0.20 mmole) were processed as in Example 279A and B to provide the titled compound. 1H NMR (500 MHz, DMSO-d6) δ12.22-12.61 (br.s, 1 H), 8.95 (s, 1 H), 8.06 (d, 1 H), 7.24 (m, 8 H), 7.03 (m, 1 H), 6.94 (m, 4 H), 6.67 (dd, 1 H), 6.49 (m, 2 H), 4.22 (m, 1 H), 4.06 (s, 2 H), 4.03 (s, 2 H), 3.91 (m, 2 H), 2.91 (s, 3 H), 2.40 (s, 3 H), 2.26 (m, 2 H), 1.90 (m, 2 H), 1.60 (m, 1 H), 1.47 (m, 2 H), 0.85 (d, 3 H), 0.81 (d, 3 H); MS (APCI+) m/z 688.7 (M+H)+.

Sources & evidence

ORD record
ord-8c1ccf50a9564236ab3e89a8637c0ab0
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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