Trifluoroacetic acid → HCID 19705437, compound

HRID 727580Notes

Reaction equation

HRID 727580 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:18]1([C:32]([CH3:34])=[CH2:33])[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]1=[O:31])[C:11]([O:13]C(C)(C)C)=[O:12])=[O:6].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:18]1([C:32]([CH3:34])=[CH2:33])[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]1=[O:31])[C:11]([OH:13])=[O:12])=[O:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19705462HCID 19705462, compound

Product 1

HCID 19705437HCID 19705437, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A cold (0° C.) solution of tert-butyl α-[2-[(3,4-difluorebenzoyl)amino]ethyl]-2-oxo-1-(2-phenylethyl)-3-(propen-2-yl)-3-pyrrolidineacetate (EXAMPLE 94, step 4; 505 mg, 0.959 mmol) in CH2Cl2 (2 mL) is treated with TFA (2 mL) and maintained at 0° C. for 30 min. The ice bath is removed, and after 1 h, the solution was diluted with CH2Cl2 and concentrated (3×). The residual oil is diluted with H2O (10 mL) and extracted into CH2Cl2 (3×25 mL). The extracts are combined, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to provide 430 mg (95%) of the title compound as a slightly yellow, amorphous solid:

Workup

  1. customThe ice bath is removed
  2. additionthe solution was diluted with CH2Cl2
  3. concentrationconcentrated (3×)
  4. additionThe residual oil is diluted with H2O (10 mL)
  5. extractionextracted into CH2Cl2 (3×25 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-246ba87ec9514ad1a3351f43af1fa6ae
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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