Trifluoroacetic acid → HCID 66684295, compound

HRID 513040Notes

Reaction equation

HRID 513040 reaction equation
[F:1][C:2]1([F:27])[CH2:6][N:5](C(OC(C)(C)C)=O)[C@@H:4]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[C:21](=[O:26])[NH:22][CH:23]([CH3:25])[CH3:24])[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:27][C:2]1([F:1])[CH2:6][NH:5][C@@H:4]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[C:21]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:26])[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66684643HCID 66684643, compound

Product 1

HCID 66684295HCID 66684295, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 4,4-difluoro-2-(5-fluoro-2-(isopropylcarbamoyl)phenyl)pyrrolidine-1-carboxylate (I-50) (203 mg, 0.525 mmol) in DCM (0.4 mL) was added TFA (1 mL). After stirring for 2 hours the mixture was concentrated to dryness, diluted with DCM, washed with saturated aqueous NaHCO3 and brine, dried over sodium sulfate and concentrated to dryness to give (R)-2-(4,4-difluoropyrrolidin-2-yl)-4-fluoro-N-isopropylbenzamide (I-51) as a pale brown solid. MS m/z 287.1 (M+H)+. 1-51 was also isolated as a racemic mixture using un-resolved 1-45A and 1-45B from Method A in the above sequence.

Workup

  1. concentrationwas concentrated to dryness
  2. additiondiluted with DCM
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3f7b88e22256419fb6e89845e3a4ab81
Source dataset
uspto-grants-2015_08
Patent number
US09102671B2

Reaction notes

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