(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone → HCID 11961984, compound

HRID 1354546Notes

Reaction equation

HRID 1354546 reaction equation
[CH2:1]([C@H:3]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)C(=O)[CH2:4]1)[CH3:2].[CH3:18][O-:19].[Na+].[CH3:21][OH:22]>CO>[F:14][C:13]([F:15])([F:16])[C:10]1[CH:9]=[CH:8][C:7]([NH:6][C@H:3]([CH2:1][CH3:2])[CH2:4][C:18]([O:22][CH3:21])=[O:19])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinoneHCID 23694274Sodium methanolate methanol

Product 1

HCID 11961984HCID 11961984, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

420 mg (1.73 mmol) of (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone produced in Example 6 was dissolved in methanol (7.0 mL) and further mixed with 668 mg (3.46 mmol) of 28 wt % sodium methoxide/methanol solution at room temperature. After stirring at the same temperature for further 1 hour, the solvent was removed by distillation under reduced pressure and 1 N hydrochloric acid (5.0 mL) was added and extraction with ethyl acetate was carried out. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, and the product was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to obtain methyl (R)-3-[4-(trifluoromethyl)phenylamino]-pentanoate as a colorless oil (459 mg, crude yield: 97%).

Workup

  1. customthe solvent was removed by distillation under reduced pressure and 1 N hydrochloric acid (5.0 mL)
  2. additionwas added
  3. extractionextraction with ethyl acetate
  4. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution
  5. dry with materialthe product was dried with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c614d635ddb24592b8094abc8786e065
Source dataset
uspto-grants-2007_05
Patent number
US07223859B2

Reaction notes

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