Trifluoroacetic acid → alpha-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic Acid

HRID 727530Notes

Reaction equation

FC(F)(F)C(O)=O.[O:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]1[CH2:19][CH2:20][CH:21]([C:29]1([CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]1=[O:42])[C:22]([O:24]C(C)(C)C)=[O:23]>C(Cl)Cl>[O:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]1[CH2:19][CH2:20][CH:21]([C:29]1([CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]1=[O:42])[C:22]([OH:24])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

Trifluoroacetic acid (2.0 mL) is added to a solution of tert-butyl α-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (282 mg, 0.507 mmol) in CH2Cl2 (4.0 mL) at 0° C. The solution is stirred for 1 hour at 0° C. A second portion of trifluoroacetic acid (2.0 mL) is added, and the solution is stirred for 30 minutes at 0° C. and for 30 minutes at room temperature. Concentration and aqueous workup (CH2Cl2, MgSO4) to give 217 mg (90%) of the title compound as a colorless oil.

Workup

stirringthe solution is stirred for 30 minutes at 0° C. and for 30 minutes at room temperature
concentrationConcentration and aqueous workup (CH2Cl2, MgSO4)

Sources & evidence

ORD record: ord-29a88d2ed1384d0fa4f9b6c2a23b4374
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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