Trifluoroacetic acid → 3-(2-Methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic Acid

HRID 727521Notes

Reaction equation

HRID 727521 reaction equation
[CH3:1][CH:2]([CH3:26])[CH2:3][C:4]1([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]1=[O:17].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][CH:2]([CH3:26])[CH2:3][C:4]1([CH2:18][C:19]([OH:21])=[O:20])[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]1=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54164883tert-Butyl 3-(2-Methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate

Product 1

HCID 197055043-(2-Methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic AcidYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (659 mg, 1.83 mmol), trifluoroacetic acid (6.5 mL) and CH2Cl2 (6.5 mL) is stirred at room temperature for 1 hour. The solution is concentrated from CH2Cl2 (3×50 mL), dissolved in 1N NaOH (10 ml), and the basic layer is extracted with Et2O (2×25 mL). The pH of the basic layer is adjusted to pH 1 with 6N HCl. The acidic layer is extracted with CH2Cl2 (2×25 mL), the combined CH2 Cl2 layers dried (MgSO4), filtered and concentrated to give 511 mg (92%) of the title compound as a colorless oil.

Workup

  1. concentrationThe solution is concentrated from CH2Cl2 (3×50 mL)
  2. dissolutiondissolved in 1N NaOH (10 ml)
  3. extractionthe basic layer is extracted with Et2O (2×25 mL)
  4. extractionThe acidic layer is extracted with CH2Cl2 (2×25 mL)
  5. dry with materialthe combined CH2 Cl2 layers dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-18ef11c0c4f54eb0ba8f621ae75f414d
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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