Sodium Hydroxide → HCID 9822766, compound

HRID 1634514Notes

Reaction equation

HRID 1634514 reaction equation
[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([C:18](=[O:31])[NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:11]=1)[C:4]([O:6]CC)=[O:5])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([C:18](=[O:31])[NH:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=2)[CH:11]=1)[C:4]([OH:6])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11004632HCID 11004632, compound

Product 1

HCID 9822766HCID 9822766, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-ethyl-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]propanoate (1.26 g, 2.88 mmol; Example 7), 15 ml of ethanol and 15 ml of 1 mol/l aqueous solution of sodium hydroxide were mixed and, after stirring for 4 hours at 50° C., the reaction mixture was concentrated under reduced pressure. The residue was dissolved in water, which was made acidic with dilute hydrochloric acid. The precipitates produced were filtered, dried and then recrystallized from ethyl acetate to obtain 1.26 g (95%) of the title compound as colorless prisms. Melting point 144.5-146.5° C.; Mass analysis m/z 409(M+); Elemental analysis C21H22F3NO4(409.40):

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. customThe precipitates produced
  4. filtrationwere filtered
  5. customdried
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-93292f2c3fb8474a988be5a931ff1221
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

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