Triethylamine → HCID 68547020, compound

HRID 1432117Notes

Reaction equation

HRID 1432117 reaction equation
CO[C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1.CCN(CC)CC.ClC(OCC(C)C)=O.[CH3:29][NH:30][CH2:31][CH:32]=[CH2:33]>C1COCC1.O>[CH2:31]([N:30]([CH3:29])[C:3](=[O:13])[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])[CH:32]=[CH2:33]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 69391N-MethylallylamineHCID 6018803-(Methoxycarbonyl)benzoic acid

Product 1

HCID 68547020HCID 68547020, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.5 g (13.9 mmol) isophthalic acid mono methyl ester in 25 ml THF, cooled at −30° C. is treated with 2.32 ml (16.9 mmol) Et3N followed by 2.0 ml (15.3 mmol) isobutyl chloroformate. After 30 min at −20° C. are added 1.4 ml (13.9 mmol) methyl allyl amine to the white suspension. After 4 h at −20° C. the mixture is poured into 50 ml water and extracted with EtOAc. The organic phase is washed with water, dried with Na2SO4 and evaporated. The residue is purified via chromatography on silica gel (EtOAc/hexane 1:2), yielding the methyl ester of the title compound. This ester is taken up in 5 ml MeOH and 5 ml 1N NaOH. After stirring for 2 h the mixture is acidified with 6 ml 1N HCl and extracted with EtOAc. The organic layer is dried with Na2SO4 and evaporated to yield the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with water
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe residue is purified via chromatography on silica gel (EtOAc/hexane 1:2)

Sources & evidence

ORD record
ord-410024acb724472e8bfd2774963dc4b9
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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