Trifluoroacetic acid → HCID 19705502, compound

HRID 727548Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH:14]([C:22]1([CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:23]1=[O:34])[C:15]([O:17]C(C)(C)C)=[O:16].C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH:14]([C:22]1([CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:23]1=[O:34])[C:15]([OH:17])=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A cold (0° C.) solution of tert-butyl α-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(phenylmethyl)-3-pyrrolidineacetate (500 mg, 0.964 mmol) in CH2Cl2 (2 ml) is treated with TFA (2 mL) and maintained at 0° C. for 1 hour, and then at room temperature for 1 hour. The solvent is removed in vacuo to give a quantitative yield of α-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-3-(2-methylpropyl)-2-oxo-1-(phenylmethyl)-3-pyrrolidineacetic acid as a gelatinous solid.

Workup

customThe solvent is removed in vacuo

Sources & evidence

ORD record: ord-edf09368bf2f430483ad3ae4180400e5
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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