Hydrochloric Acid → HCID 58031818, compound

HRID 240265Notes

Reaction equation

HRID 240265 reaction equation
[CH:1]([C:4]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:5]=1[O:6][CH:7]([CH3:11])[C:8]([OH:10])=O)([CH3:3])[CH3:2].C(N(CC)CC)C.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([O:38][CH3:39])[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:27][CH:26]=1.Cl>S(Cl)(Cl)=O.O>[CH:1]([C:4]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:5]=1[O:6][CH:7]([CH3:11])[C:8]([NH:24][C:25]1[CH:26]=[CH:27][C:28]([CH:31]([O:38][CH3:39])[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][CH:30]=1)=[O:10])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 38671632-(2-isopropyl-5-methylphenoxy)propanoic acidHCID 66628645HCID 66628645, compound

Product 1

HCID 58031818HCID 58031818, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 150 mg (0.67 mmol) of 2-(2-isopropyl-5-methylphenoxy)propionic acid in 1 ml of thionyl chloride was boiled under reflux under argon for 30 minutes. The reaction mixture was concentrated, admixed with 2 ml of toluene and concentrated again. The residue was dissolved in 3 ml of acetonitrile under argon, admixed with 940 μl (0.67 mmol) of triethylamine and a solution of 150 mg (0.67 mmol) of ethyl 3-(4-aminophenyl)-3-methoxypropionate and stirred at room temperature for 30 minutes. The reaction mixture was diluted with water, adjusted to pH=6-7 with 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under high vacuum. This gave 287 mg of ethyl 3-{4-[2-(2-isopropyl-5-methylphenoxy)propionylamino]phenyl}-3-methoxypropionate.

Workup

  1. temperatureunder reflux under argon for 30 minutes
  2. concentrationThe reaction mixture was concentrated
  3. concentrationconcentrated again
  4. dissolutionThe residue was dissolved in 3 ml of acetonitrile under argon
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-9aad260b020d48248a50c503e64789d4
Source dataset
uspto-grants-2014_02
Patent number
US08648038B2

Reaction notes

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