Methanol → HCID 69338213, compound

HRID 2086179Notes

Reaction equation

HRID 2086179 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([CH2:10][CH2:11][C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)([CH3:9])C(O)=O)[CH3:2].C([N:20]([CH2:23]C)CC)C.[CH3:25][OH:26].[OH2:27]>C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:17])[C:5]([NH:20][C:23]([O:26][CH3:25])=[O:27])([CH3:9])[CH2:10][CH2:11][C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 69338235HCID 69338235, compound

Product 1

HCID 69338213HCID 69338213, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Methyl-2-(2-thienyl)ethylmalonic acid monoethylester (19.0 g, 74.3 mmol) obtained in Example 1(b) was dissolved in benzene (450 ml), and triethylamine (11.4 ml, 81.7 mmol) and diphenylphosphoric acid azide (17.6 ml, 81.7 mmol) were added thereto, and after stirring for 10 minutes at room temperature, the reaction solution was stirred for another 1.5 hours at 80° C. Subsequently, methanol (60.3 ml, 1.49 mol) was slowly added dropwise thereto for 30 minutes at 80° C. followed by stirring for 8 hours. The reaction mixture was poured into water (500 ml) and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was concentrated in vacuo, and the residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=8:1-4:1) to afford the title compound (14.7 g, 69% yield) as a colorless oil.

Workup

  1. stirringthe reaction solution was stirred for another 1.5 hours at 80° C
  2. waitfor 30 minutes at 80° C. followed
  3. stirringby stirring for 8 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe solvent was concentrated in vacuo
  8. customthe residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=8:1-4:1)

Sources & evidence

ORD record
ord-994ce578cfd448639f2e4f07fdf36cfd
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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