Lithium Hydroxide → HCID 57931285, compound

HRID 2261860Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To an ambient temperature solution of {4-[({4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-methyl-amino)-methyl]-phenyl}-acetic acid methyl ester (81 mg, 0.143 mmol) in dioxane (2 mL) is added a solution of lithium hydroxide (215 μL, 0.429 mmol, 2.0N in water). The reaction mixture is heated to 50° C. The reaction is concentrated and the residue is partitioned between Et2O and water. The aqueous layer pH is adjusted to approximately 7 and the aqueous layer 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 (75 mg, 95%). ES/MS m/e (35Cl) 552.0 (M+1).

Workup

concentrationThe reaction is concentrated
customthe residue is partitioned between Et2O and water
extractionthe aqueous layer is 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-3bddb6f15171409ba5bd1e9f5b179b8b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846960B2

Reaction notes

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