Lithium hydroxide, monohydrate → HCID 44546375, compound

HRID 1094367Notes

Reaction equation

HRID 1094367 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=2)[C:10]([C@@H:12]([O:19]C(=O)C)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].O.[OH-].[Li+]>O1CCCC1.O>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:27][N:26]=2)[C:10](=[O:11])[C@@H:12]([OH:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 44546441HCID 44546441, compound

Product 1

HCID 44546375HCID 44546375, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 116 mg (0.25 mmol) acetic acid (S)-{(3,4-dimethyl-phenyl)-[2-(5-trifluoromethyl-pyridin-2-yl)-ethyl]-carbamoyl}-phenyl-methyl ester in 1.2 mL tetrahydrofuran were added 0.6 mL water and 11.4 mg (0.27 mmol) lithium hydroxide monohydrate. The mixture was stirred at room temperature overnight. 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 0.098 g (93%) of the title compound as a colorless oil. MS(m/e): 429.2 [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-9e84607c5afe4ca7a014fa60dc391a19
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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