Lithium Hydroxide → HCID 23582413, compound

Reaction equation

[OH-].[Li+].C[O:4][C:5](=[O:28])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][C:17]2[CH:26]=[CH:25][C:20]3[N:21]=[N:22][N:23]([CH3:24])[C:19]=3[CH:18]=2)[C:8]=1[CH3:27]>C1COCC1.O.C(Cl)Cl>[CH3:27][C:8]1[N:9]([CH2:16][C:17]2[CH:26]=[CH:25][C:20]3[N:21]=[N:22][N:23]([CH3:24])[C:19]=3[CH:18]=2)[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:15]2[C:7]=1[CH2:6][C:5]([OH:28])=[O:4]

Participants

Procedure

1 M Lithium hydroxide (116 μl) is added to a cooled (0° C.) solution of [2-methyl-1-(3-methyl-3H-benzotriazol-5-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (0.041 g, 0.116 mmol) in THF/water (4 ml of a 1:1 mixture). After stirring at room temperature for 4 hours, the reaction mixture is diluted with DCM (3 ml) and stirred vigorously for 10 minutes. The resulting mixture is passed through a phase separation cartridge and the aqueous portion is acidified to pH 1-3 with 1M HCl. This portion is extracted with DCM (2×3 ml) and the organic extracts are combined and concentrated in vacuo to yield the titled compound as a white solid. (MH+336)