Lithium Hydroxide → HCID 59054528, compound

HRID 1748214Notes

Reaction equation

HRID 1748214 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=2[CH2:20][O:21][CH:22]2[CH2:28][CH:27]3[N:29]([C:30]4[S:31][C:32]5[CH:38]=[C:37]([C:39]([NH:41][CH2:42][C:43]([O:45]C)=[O:44])=[O:40])[CH:36]=[CH:35][C:33]=5[N:34]=4)[CH:24]([CH2:25][CH2:26]3)[CH2:23]2)[CH2:3][CH2:2]1.[Li+].[OH-]>O.O1CCOCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:17])([F:18])[F:19])[C:5]=2[CH2:20][O:21][CH:22]2[CH2:28][CH:27]3[N:29]([C:30]4[S:31][C:32]5[CH:38]=[C:37]([C:39]([NH:41][CH2:42][C:43]([OH:45])=[O:44])=[O:40])[CH:36]=[CH:35][C:33]=5[N:34]=4)[CH:24]([CH2:25][CH2:26]3)[CH2:23]2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 67982976HCID 67982976, compound

Product 1

HCID 59054528HCID 59054528, compound

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-(2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxamido)acetate was subjected to a solution of 4N LiOH in water (2 mL) and dioxane (2 ml) and stirred for 2 hours. The solvent was reduced in vacuo and the mixture diluted with 5% citric acid (10 ml) and extracted with ethyl acetate (2×8 mL). The organics were combined and dried (MgSO4) then evaporated in vacuo. The product was purified with flash silica chromatography with methanol/dichloromethane with a 0-40% gradient to give the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate (2×8 mL)
  2. dry with materialdried (MgSO4)
  3. customthen evaporated in vacuo
  4. customThe product was purified with flash silica chromatography with methanol/dichloromethane with a 0-40% gradient

Sources & evidence

ORD record
ord-3c41088b00184574805e85a05fcc7367
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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