Lithium Hydroxide → HCID 24862900, compound

HRID 424841Notes

Reaction equation

C[O:2][C:3](=[O:42])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[C:14]([CH3:40])=[N:15][C:16]([O:19][CH2:20][C:21]3[N:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][C:36]([F:39])([F:38])[F:37])[N:23]=[N:24][C:25]=3[CH:26]([CH3:28])[CH3:27])=[CH:17][CH:18]=2)[CH3:12])=[CH:6][C:5]=1[CH3:41].[OH-].[Li+]>O1CCOCC1>[CH:26]([C:25]1[N:24]=[N:23][N:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][C:36]([F:39])([F:38])[F:37])[C:21]=1[CH2:20][O:19][C:16]1[N:15]=[C:14]([CH3:40])[C:13]([N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:42])=[O:2])=[C:5]([CH3:41])[CH:6]=2)[CH3:12])=[CH:18][CH:17]=1)([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-[({6-[5-isopropyl-3-(2-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-pyridin-3-yl}-methyl-amino)-methyl]-2-methyl-benzoic acid methyl ester (147 mg, 0.251 mmol) in dioxane (2 mL) is treated with a solution of lithium hydroxide (378 mL, 0.756 mmol, 2.0N in water) and heated to 50° C. After 2 h, the reaction is concentrated and the residue is partitioned between Et2O and water. The aqueous layer is adjusted to pH ˜7 and is extracted with a second portion of Et2O. The combined organic layers are washed with water, dried (MgSO4), filtered, and concentrated to yield the title compound (138 mg, 97%). LC/MS (ES+): 570.0, 100%.

Workup

concentrationthe reaction is concentrated
customthe residue is partitioned between Et2O and water
extractionis extracted with a second portion of Et2O
washThe combined organic layers are washed with water
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-e8daefd7959e4c489421d15ad13a3f9f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106077B2

Reaction notes

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