Sodium Hydroxide → HCID 13799300, compound

HRID 1086920Notes

Reaction equation

HRID 1086920 reaction equation
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([NH:21][C:22](=[O:27])[C:23]([O:25]C)=[O:24])[C:16]([CH3:20])=[CH:17][C:18]=2[Br:19])=[C:6]([CH2:30][CH2:31][C:32]([F:35])([F:34])[F:33])[C:5]=1[OH:36])(=[O:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([NH:21][C:22](=[O:27])[C:23]([OH:25])=[O:24])[C:16]([CH3:20])=[CH:17][C:18]=2[Br:19])=[C:6]([CH2:30][CH2:31][C:32]([F:33])([F:34])[F:35])[C:5]=1[OH:36])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13799299HCID 13799299, compound

Product 1

HCID 13799300HCID 13799300, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 1.75 g (3 mmol) of methyl N-{{3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-4-bromo-6-methyl-phenyl}}-oxamate (Example 2) in 30 ml of methanol and 3.2 ml of N sodium hydroxide solution is refluxed for 60 minutes. The reaction mixture is concentrated under reduced pressure, the residue is dissolved in acetone and dilute sodium hydroxide solution and the solution is acidified with dilute hydrochloric acid. The product which has precipitated is filtered off and washed neutral with water. N-{{3-{3-[4-Acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-4-bromo-6-methyl-phenyl}}-oxamic acid of melting point 207°-209° is thus obtained.

Workup

  1. temperatureis refluxed for 60 minutes
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in acetone
  4. customThe product which has precipitated
  5. filtrationis filtered off
  6. washwashed neutral with water

Sources & evidence

ORD record
ord-9eba9fae951b4c94b397ea4a30cb74fa
Source dataset
uspto-grants-1991_07
Patent number
US05032606

Reaction notes

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