Trifluoroacetic acid → HCID 21936992, compound

HRID 746483Notes

Reaction equation

HRID 746483 reaction equation
FC(F)(F)C(O)=O.[C:8]1([CH:14]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:15][CH2:16][N:17]([C:31]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=2)=[O:32])[CH:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl>[C:44]1([CH:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:15][CH2:16][N:17]([CH:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)[C:31]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:42])([F:41])[F:43])[CH:35]=2)=[O:32])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10121014HCID 10121014, compound

Product 1

HCID 21936992HCID 21936992, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.6 ml (21 mmol, 20 eq.) of trifluoroacetic acid is added to a solution of tert-butyl 4-((3,3-diphenylpropyl) {[3-(trifluoromethyl)anilino]carbonyl}amino)-1-piperidine carboxylate (600 mg, 1.04 mmol) in dichloromethane. The reaction medium is agitated for 90 minutes then concentrated. Dichloromethane is added and the organic phase is washed with a saturated solution of sodium bicarbonate, dried over magnesium sulphate, filtered and concentrated under vacuum in order to isolate 490 mg (yield=98%) of a white foam.

Workup

  1. concentrationthen concentrated
  2. additionDichloromethane is added
  3. washthe organic phase is washed with a saturated solution of sodium bicarbonate
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum in order

Sources & evidence

ORD record
ord-82afdb8f177745119400631b582df984
Source dataset
uspto-grants-2008_07
Patent number
US07393861B2

Reaction notes

Loading…