Lithium hydroxide, monohydrate → HCID 44545786, compound

HRID 1094397Notes

Reaction equation

HRID 1094397 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([N:12]([CH2:26][CH2:27][C:28]3[CH:29]=[N:30][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:33]=3)[C:13]([C@@H:15]([O:22]C(=O)C)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:14])=[CH:9][CH:10]=2)[C:5]([CH3:38])=[N:4]1)[CH3:2].O.[OH-].[Li+]>O1CCCC1.O>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([N:12]([CH2:26][CH2:27][C:28]3[CH:29]=[N:30][C:31]([C:34]([F:36])([F:35])[F:37])=[CH:32][CH:33]=3)[C:13](=[O:14])[C@@H:15]([OH:22])[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:9][CH:10]=2)[C:5]([CH3:38])=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58007508HCID 58007508, compound

Product 1

HCID 44545786HCID 44545786, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acetic acid (S)-{(1-ethyl-3-methyl-1H-indazol-5-yl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-carbamoyl}-phenyl-methyl ester (150 mg, 0.286 mmol) in tetrahydrofuran (2.0 mL) were added 1.0 mL water and 20.0 mg (0.84 mmol) lithium hydroxide monohydrate. The mixture was stirred at room temperature for 2 h. The mixture was diluted with water and extracted 3 times with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 89 mg (65%) of the title compound as a colourless oil. MS(m/e): 483.1 [M+H]+.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
  6. customformed from heptane and ethylacetate

Sources & evidence

ORD record
ord-a21f8b66f04246c48a8e7dd016adf842
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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