Citric Acid → HCID 86643333、化合物

反応式

[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23]([O:25]C)=[O:24])=[CH:21][N:22]=2)[CH2:14][C@H:13]1[O:27][CH3:28])=[O:10].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=2)[CH2:14][C@H:13]1[O:27][CH3:28])=[O:10]

参加物

反応条件

温度: 50 °C

実験手順

Cis(±)methyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate (Example 1; 200 mg) was dissolved in THF (50 ml). 2N LiOH (100 ml) was added and the mixture was heated at 50° C. for 18 h. The reaction mixture was cooled to ambient and acidified with 20% aqueous citric acid. The aqueous phase was extracted with EtOAc and the organic phase was washed with water, brine, dried over Na2SO4. The organic phase was concentrated in vacuo and triturated with diethyl ether to give the title compound as an off white solid. (164 mg). MS (ES) MH+: 433, 431 for C16H18Cl2N4O4S; NMR: 1.87 (m, 2H), 2.28 (s, 3H), 3.32 (m, 6H), 3.63 (s, 1H), 3.87 (m, 1H), 4.45 (m, 2H), 7.04 (d, 1H), 7.90 (s, 1H), 11.97 (s, 1H), 12.30 (s, 1H).