methyl L-prolinate hydrochloride → HCID 21130138, compound

HRID 1370926Notes

Reaction equation

HRID 1370926 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:40]=[CH:39][C:25]([O:26][C:27]2[CH:32]=[CH:31][C:30]([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:43][C:44](=[O:50])[C@@H:45]1[CH2:49][CH2:48][CH2:47][NH:46]1>>[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]([CH2:33][CH2:34][CH2:35][C:36]([N:46]3[CH2:47][CH2:48][CH2:49][C@H:45]3[C:44]([OH:43])=[O:50])=[O:37])=[CH:31][CH:32]=2)=[CH:39][CH:40]=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 2733200methyl L-prolinate hydrochlorideHCID 185122134-(4-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenyl)butanoic Acid

Product 1

HCID 21130138HCID 21130138, compound

Procedure

The product from Example 100 (56 mg, 0.1 mmole) and L-Proline methyl ester hydrochloride (33 mg, 0.2 mmole) were processed as in Examples 213A and 224B to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ11.66-13.14 (br.s, 1 H), 8.95 (s, 1 H), 7.26 (m, 6 H), 7.18 (m, 3 H), 7.04 (m, 1 H), 6.96 (m, 2 H), 6.88 (m, 4 H), 4.22 (dd, 1 H), 4.03 (d, 4 H), 3.46 (m, 2 H), 2.91 (s, 3 H), 2.58 (t, 2 H), 2.39 (s, 3 H), 2.27 (t, 2 H), 1.97-2.24 (m, 2 H), 1.70-1.95 (m, 4 H); MS (APCI+) m/z 656 (M+H)+.

Sources & evidence

ORD record
ord-650b72d1305e4fda9841d245c90d266a
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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