Trifluoroacetic acid → HCID 19705446, compound

HRID 727569Notes

Reaction equation

HRID 727569 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][CH:14]([C:22]2([CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]2=[O:35])[C:15]([O:17]C(C)(C)C)=[O:16])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>ClCl.C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH:12][CH2:13][CH:14]([C:22]2([CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]2=[O:35])[C:15]([OH:17])=[O:16])(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19705455HCID 19705455, compound

Product 1

HCID 19705446HCID 19705446, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 24526ChlorineSolvent

Conditions

Temperature
0 °C

Procedure

A cold (0° C.) solution of tert-butyl α-[[[(4-methoxyphenyl)sulfonyl]amino]methyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (374 mg, 0.669 mmol) in CH2 Cl2 (2 mL) is treated with TFA (2 mL). The solution is maintained at 0° C. for 40 min and then allowed to warm to room temperature under N2. After 1.5 hours, the solution is diluted with CH2Cl2 and stripped (5×). The residual foam is diluted with H2O (5 mL) and extracted into CH2Cl2 (3×20 mL). The extracts are combined, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to provide 301 mg (90%) of the title compound as a white, amorphous solid:

Workup

  1. temperatureto warm to room temperature under N2
  2. extractionextracted into CH2Cl2 (3×20 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57b64a24f44d40bcb41e7fb0e92a3c9e
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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