Lithium Hydroxide → HCID 86707529, compound

HRID 339032Notes

Reaction equation

HRID 339032 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([C:18]1[N:22]3[CH:23]=[C:24]([C@@H:27]([N:32]4[CH2:36][CH2:35][C@H:34]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:33]4)[C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:26][C:21]3=[N:20][N:19]=1)[CH:14]=[CH:13]2)(=O)C.[OH-].[Li+]>CO>[F:30][C:28]([F:29])([F:31])[C@H:27]([N:32]1[CH2:36][CH2:35][C@H:34]([NH:37][C:38](=[O:39])[O:40][C:41]([CH3:44])([CH3:42])[CH3:43])[CH2:33]1)[C:24]1[CH:25]=[CH:26][C:21]2[N:22]([C:18]([C:15]3[CH:14]=[CH:13][C:12]4[C:17](=[C:8]([O:7][CH2:6][CH2:5][OH:4])[CH:9]=[CH:10][CH:11]=4)[N:16]=3)=[N:19][N:20]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86707528HCID 86707528, compound

Product 1

HCID 86707529HCID 86707529, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(2-(6-((R)-1-((S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)ethyl acetate (0.47 g, 0.76 mmol) in methanol (5 mL) was added lithium hydroxide (2M; 1.9 mL, 0.76 mmol) and the mixture allowed to stir at ambient temperature for 1 hour. The reaction mixture was extracted with dichloromethane (2×30 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography on C18 (0-100% acetonitrile/water) to provide the title compound (0.40 g, 92%).

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (2×30 mL)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by reverse phase chromatography on C18 (0-100% acetonitrile/water)

Sources & evidence

ORD record
ord-9da37fba5fe6477dabf75fec935975e3
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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