Trifluoroacetic acid → alpha-Methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic Acid

HRID 727524Notes

Reaction equation

C(O)(C(F)(F)F)=O.[CH3:8][CH:9]([C:17]1([CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]1=[O:30])[C:10]([O:12]C(C)(C)C)=[O:11]>C(Cl)Cl>[CH3:8][CH:9]([C:17]1([CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]1=[O:30])[C:10]([OH:12])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

TFA (10.0 mL) is added to a solution of tert-butyl α-methyl-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (780 mg, 2.09 mmol) and CH2Cl2 (10 mL) at 0° C. The solution is stirred for 2.5 hours at 0° C. and 1.5 hours at room temperature. After concentration, the residue is partitioned between EtOAc and water. The organic layer is extracted several times with 10% NaOH, the combined basic layers acidified (4N HCl), and the acidic layers extracted several times with CH2Cl2. The CH2Cl2 layers are dried (MgSO4), filtered, and concentrated to provide 79 mg (12%) of the title compound as a white solid (mp 94°-95° C.).

Workup

concentrationAfter concentration
customthe residue is partitioned between EtOAc and water
extractionThe organic layer is extracted several times with 10% NaOH
extractionthe acidic layers extracted several times with CH2Cl2
dry with materialThe CH2Cl2 layers are dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-53ff07e427bf49fc874f43866cd44dcf
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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