Sodium Hydroxide → 1,1-dimethylethyl (1RS,2RS)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethylcarbamate

HRID 1610186Notes

Reaction equation

HRID 1610186 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12]C(=O)[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]2[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH:9]([NH:10][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 698294291,1-Dimethylethyl(4rs,5rs)-5-(4-fluorophenyl)-2-oxo-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidine-3-carboxylate

Product 1

HCID 865932161,1-dimethylethyl (1RS,2RS)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethylcarbamateYield 77.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 1,1-dimethylethyl (4RS,5SR)-5-(4-fluorophenyl)-2-oxo-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidine-3-carboxylate (4.0 g, 9.10 mmol) in methanol (22 ml) was gradually added a solution of sodium hydroxide (0.44 g, 10.92 mmol) in methanol (22 ml) under ice-cooling. The reaction solution was stirred for 3 hrs., diluted with 1N hydrochloric acid (12 ml) and water (100 ml), and extracted with ethyl acetate (100 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) and recrystallized from ethyl acetate-hexane to give the title compound (2.90 g, 77%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (100 ml×2)
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3f874624e19646b1bb9caec1feef23b3
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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