2-Methylaziridine → HCID 23114148, compound

HRID 2376330Notes

Reaction equation

HRID 2376330 reaction equation
[CH:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][C:9]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:10]=2[O:11][CH2:12][C:13]([OH:15])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH3:30][CH:31]1[NH:33][CH2:32]1.C(N(CC)CC)C>C1COCC1.CN(C=O)C.O>[CH:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][C:9]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:10]=2[O:11][CH2:12][C:13]([N:33]2[CH2:32][CH:31]2[CH3:30])=[O:15])=[CH:6][CH:5]=1)([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 63772-MethylaziridineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 23113955HCID 23113955, compound

Product 1

HCID 23114148HCID 23114148, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of (2-(4-isopropylbenzyl)-3,5-dimethylphenoxy)acetic acid obtained in Reference Example 157 (9.00 g, 28.8 mmol) in THF (90 mL) was added dropwise oxalylchloride (3.77 mL, 43.2 mmol) with ice-cooling, and was then added DMF (four drops), and then the mixture was stirred for 30 minutes. The reaction solution was stirred at room temperature for 30 minutes, and the solvent was distilled off under reduced pressure. To a solution of propyleneimine (1.97 g, 34.6 mmol) and triethylamine (4.82 mL, 34.6 mmol) in THF (80 mL) was added dropwise the obtained solution of acid chloride in THF (100 mL) with ice-cooling. The mixture was stirred for 30 minutes, and then was warmed to room temperature, and water was added to the reaction solution, which was extracted with ethyl acetate. The combined organic layer was washed with a saturated brine, dried over sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:3) to obtain 10.0 g (yield 99%) of the title compound. Oily matter.

Workup

  1. temperaturecooling
  2. distillationthe solvent was distilled off under reduced pressure
  3. temperaturecooling
  4. stirringThe mixture was stirred for 30 minutes
  5. temperaturewas warmed to room temperature
  6. extractionwas extracted with ethyl acetate
  7. washThe combined organic layer was washed with a saturated brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:3)

Sources & evidence

ORD record
ord-e8479396218947ec81cbd2a9209f444c
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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