Hydrochloric Acid → HCID 58031819, compound

HRID 240255Notes

Reaction equation

HRID 240255 reaction equation
[Br:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][C:7]([CH3:31])([CH3:30])[C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH:21]([C:26]([O:28]C)=[O:27])[C:22]([O:24]C)=[O:23])[C:18]#[C:19][CH3:20])=[CH:13][CH:12]=2)=[O:9])=[C:4]([Cl:34])[CH:3]=1.Cl>C(#N)C.[OH-].[Na+]>[Br:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][C:7]([CH3:30])([CH3:31])[C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([CH:17]([CH:21]([C:26]([OH:28])=[O:27])[C:22]([OH:24])=[O:23])[C:18]#[C:19][CH3:20])=[CH:15][CH:16]=2)=[O:9])=[C:4]([Cl:34])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58031790HCID 58031790, compound

Product 1

HCID 58031819HCID 58031819, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 180 mg of dimethyl 2-(1-{4-[2-(4-bromo-2-chlorophenoxy)-2-methylpropionylamino]phenyl}but-2-ynyl)malonate in 5 ml of acetonitrile and 3.5 ml of 1 N sodium hydroxide solution (aq) was stirred at room temperature for 18 h. The reaction mixture was adjusted to pH=1 with 1 N HCl (aq) and then extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under high vacuum. This gave 171 mg of 2-(1-{4-[2-(4-bromo-2-chlorophenoxy)-2-methylpropionylamino]phenyl}but-2-ynyl)malonic acid in quantitative yield.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-41da3ca54bfc4c85ae3c916476bcd4f2
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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