Trifluoroacetic acid → 3-(2-Methylpropyl)-2-oxo-1-(2-phenylethyl)-alpha-[2-(2-thienylthio)ethyl]-3-pyrrolidineacetic Acid

HRID 727535Notes

Reaction equation

HRID 727535 reaction equation
[CH3:1][CH:2]([CH3:34])[CH2:3][C:4]1([CH:18]([CH2:26][CH2:27][S:28][C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)[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]([CH3:34])[CH2:3][C:4]1([CH:18]([CH2:26][CH2:27][S:28][C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)[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 19705522tert-Butyl 3-(2-Methylpropyl)-2-oxo-1-(2-phenylethyl)-alpha-[2-(2-thienylthio)ethyl]-3-pyrrolidineacetate

Product 1

HCID 197054693-(2-Methylpropyl)-2-oxo-1-(2-phenylethyl)-alpha-[2-(2-thienylthio)ethyl]-3-pyrrolidineacetic AcidYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-α-[2-(2-thienylthio)ethyl]-3-pyrrolidineacetate (338 mg, 0.674 mmol), trifluoroacetic acid (3 mL), and CH2Cl2 (3 mL) is stirred at 0° C. for 15 minutes and at room temperature for 1.5 hour. Concentration and aqueous workup (CH2Cl2, MgSO4) gives 287 mg (96%) of the title compound as a colorless oil.

Workup

  1. concentrationConcentration and aqueous workup (CH2Cl2, MgSO4)

Sources & evidence

ORD record
ord-ec60b4947d5c4e5a9970e75a4a9ef964
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

Loading…