Lithium hydroxide, monohydrate → (S)-2-Hydroxy-2-phenyl-N-quinolin-3-yl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-acetamide

HRID 1094441Notes

Reaction equation

HRID 1094441 reaction equation
[C:1]1([C@H:7]([O:33]C(=O)C)[C:8](=[O:32])[N:9]([C:22]2[CH:23]=[N:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>O1CCCC1.O>[OH:33][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([N:9]([C:22]1[CH:23]=[N:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=1)=[O:32]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58007583HCID 58007583, compound

Product 1

HCID 58007601(S)-2-Hydroxy-2-phenyl-N-quinolin-3-yl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 155 mg acetic acid (S)-phenyl-{quinolin-3-yl-[2-(4-trifluoromethyl-phenyl)-ethyl]-carbamoyl}-methyl ester in tetrahydrofuran (6.0 mL) were added 3.0 mL water and 20 mg 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 the title compound. MS(m/e): 451.1 [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-52c382e7ac1646bb97ba933a800aa5c5
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

Loading…