Hydrochloric Acid → HCID 56593458, compound

HRID 240261Notes

Reaction equation

HRID 240261 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][CH:31]=1)[O:7][CH:8]([CH3:28])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:25]#[C:26][CH3:27])[CH2:19][C:20]([O:22]CC)=[O:21])=[CH:14][CH:13]=1)=[O:10])([CH3:3])[CH3:2].O.Cl>C(#N)C.[OH-].[Na+]>[CH:1]([C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][CH:31]=1)[O:7][CH:8]([CH3:28])[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]([C:25]#[C:26][CH3:27])[CH2:19][C:20]([OH:22])=[O:21])=[CH:16][CH:17]=1)=[O:10])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58031811HCID 58031811, compound

Product 1

HCID 56593458HCID 56593458, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 156 mg of ethyl 3-{4-[2-(3-isopropylphenoxy)propionylamino]phenyl}-hex-4-ynoate in 7 ml of acetonitrile and 7 ml of 1 N NaOH (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 109 mg of 3-{4-[2-(3-isopropylphenoxy)propionylamino]phenyl}hex-4-ynoic acid in 37% yield over the two stages.

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-456a7fcf2e9e4f659d704775ca95567a
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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