Lithium hydroxide, monohydrate → HCID 44546312, compound

HRID 1094353Notes

Reaction equation

HRID 1094353 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:10]([CH2:24][CH2:25][C:26]2[CH:27]=[N:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=2)[C:11]([C@@H:13]([O:20]C(=O)C)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])[CH:6]=[CH:7][C:8]=1[CH3:9].O.[OH-].[Li+]>O1CCCC1.O>[OH:20][C@@H:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:11]([N:10]([C:5]1[CH:6]=[CH:7][C:8]([CH3:9])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:24][CH2:25][C:26]1[CH:27]=[N:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=1)=[O:12]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58007541HCID 58007541, compound

Product 1

HCID 44546312HCID 44546312, compoundYield 9.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acetic acid (S)-{(3-methoxy-4-methyl-phenyl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-carbamoyl}-phenyl-methyl ester (155 mg, 0.32 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 13 mg (9%) of the title compound as a colourless oil. MS(m/e): 445.1 [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-af5ad7d543014392a5e15ef8664285b7
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

Loading…