Hydrochloric Acid → HCID 58031810, compound

HRID 240258Notes

Reaction equation

HRID 240258 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][CH:35]=1)[O:8][CH:9]([CH3:32])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH:23]([C:28]([O:30]C)=[O:29])[C:24]([O:26]C)=[O:25])[C:20]#[C:21][CH3:22])=[CH:15][CH:14]=1)=[O:11])([CH3:4])([CH3:3])[CH3:2].O.Cl>C(#N)C.[OH-].[Na+]>[C:1]([C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][CH:35]=1)[O:8][CH:9]([CH3:32])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH:23]([C:24]([OH:26])=[O:25])[C:28]([OH:30])=[O:29])[C:20]#[C:21][CH3:22])=[CH:15][CH:14]=1)=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58031792HCID 58031792, compound

Product 1

HCID 58031810HCID 58031810, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 323 mg (0.67 mmol) of dimethyl 2-(1-{4-[2-(3-tert-butylphenoxy)-propionylamino]phenyl}but-2-ynyl)malonate in 7 ml of acetonitrile and 6.7 ml of 1 N sodium hydroxide solution (aq) was stirred at room temperature for 18 h. The reaction mixture was admixed with water and 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 304 mg of 2-(1-{4-[2-(3-tert-butylphenoxy)propionylamino]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-11b167cbaa5c44d6a2b0d84b52132821
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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