Lithium Hydroxide → 17-[2-(2-Cyclohexylthiazol-4-yl)-7-methoxy-8-methylquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid

HRID 531369Notes

Reaction equation

[Li+].[OH-].C([O:5][C:6]([C:8]12[CH2:25][CH:24]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH3:26])[C:16](=[O:27])[CH:15]1[CH:11]([CH2:12][CH:13]([O:28][C:29]3[C:38]4[C:33](=[C:34]([CH3:41])[C:35]([O:39][CH3:40])=[CH:36][CH:37]=4)[N:32]=[C:31]([C:42]4[N:43]=[C:44]([CH:47]5[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]5)[S:45][CH:46]=4)[CH:30]=3)[CH2:14]1)[C:10](=[O:53])[NH:9]2)=[O:7])C>CO.C1COCC1.O>[CH:47]1([C:44]2[S:45][CH:46]=[C:42]([C:31]3[CH:30]=[C:29]([O:28][CH:13]4[CH2:12][CH:11]5[CH:15]([C:16](=[O:27])[N:17]([CH3:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH:23][CH:24]6[C:8]([C:6]([OH:7])=[O:5])([NH:9][C:10]5=[O:53])[CH2:25]6)[CH2:14]4)[C:38]4[C:33](=[C:34]([CH3:41])[C:35]([O:39][CH3:40])=[CH:36][CH:37]=4)[N:32]=3)[N:43]=2)[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]1

Participants

Conditions

Temperature: 50 °C

Procedure

An aqueous solution of LiOH (1M, 5 mL) was added to a solution of 17-[2-(2-cyclohexylthiazol-4-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester (121) in MeOH (10 mL), THF (20 mL) and water (5 mL). The resulting solution was stirred at 50° C. for 19 h. Then, the pH of the reaction mixture was adjusted to 6 with myriatic acid (3M, 1.7 mL). The resulting solution was evaporated on silica and purified by column chromatography (AcOEt/MeOH/AcOH, 74:25:1) to give 273 mg (95%) of the title compound 122 as a white powder: m/z=687 (M+H)+.

Workup

customThe resulting solution was evaporated on silica
custompurified by column chromatography (AcOEt/MeOH/AcOH, 74:25:1)

Sources & evidence

ORD record: ord-4551df88067b4934811257b2a2a894b8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353103B2

Reaction notes

Loading…