Isopropyl L-methionate hydrochloride → [4-(3-Pyridyloxymethyl)-2-phenylbenzoyl]methionine isopropyl ester
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=2)[CH:2]=1.Cl.[CH:25]([O:28][C:29](=[O:36])[C@H:30]([CH2:32][CH2:33][S:34][CH3:35])[NH2:31])([CH3:27])[CH3:26]>>[CH:25]([O:28][C:29](=[O:36])[C@H:30]([CH2:32][CH2:33][S:34][CH3:35])[NH:31][C:13](=[O:14])[C:12]1[CH:16]=[CH:17][C:9]([CH2:8][O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:10][C:11]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([CH3:27])[CH3:26]Participants
3
Procedure
The desired compound was prepared by coupling of 4-(3-pyridyloxymethyl)-2-phenylbenzoic acid, prepared as in Example 228D with methionine isopropyl ester hydrochloride, prepared as in Example 229B using the procedure of Example 186C. 1H NMR (300 MHz, CD3OD) δ 8.70 (d, 1H), 8.46 (d, 1H), 8.31 (ddd, 1H), 8.01 (dd, 1H), 7.58 (m, 3H), 7.33-7.47 (m, 5H), 5.45 (s, 2H), 5.00 (heptet, 1H), 4.44 (m, 1H), 2.00-2.24 (m, 2H), 2.01 (s, 3H), 1.96 (m, 1H), 1.77 (m, 1H), 1.24 (d, 3H), 1.22 (d, 3H). MS (CI NH3) m/e 479 (M+H)+, 451, 419, 320, 288, 192. Anal calcd for C27H31ClN2O4S (+0.60 H2O): C, 61.67; H, 6.17; N, 5.33. Found: C, 61.67; H, 6.17; N, 5.33.
Sources & evidence
- ORD record
- ord-ca3d9ed960074783a76c4c869899d7b2
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06693123B2
Reaction notes
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