Trifluoroacetic acid → HCID 11414215, compound

HRID 1883480Notes

Reaction equation

HRID 1883480 reaction equation
C([O:5][C:6](=[O:23])[CH:7]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH:7]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:6]([OH:23])=[O:5])=[CH:14][CH:13]=1)#[N:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11324462HCID 11324462, compound

Product 1

HCID 11414215HCID 11414215, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-cyanophenyl)-2-(R,S)-cyclohexyl-propionic acid t-butyl ester (8.2 g, 26.2 mmol) in dichloromethane (70 ml) was added trifluoroacetic acid (14.1 ml, 183.0 mmol) with stirring at room temperature. A gentle gas evolution ensued. After 69 h, solvent and excess trifluoroacetic acid were evaporated under reduced pressure. The solid was taken up in ethyl acetate and washed with water and brine, then dried (magnesium sulfate), filtered, and evaporated to dryness. The crude product was dissolved in methanol, treated with decolorizing carbon, filtered through celite, and concentrated. The resultant solid was recrystallized from toluene to afford the desired product as an off-white powder (6.83 g, 58%). mp.: 115-117° C., MS m/z: 258 (M+H)+.

Workup

  1. customsolvent and excess trifluoroacetic acid were evaporated under reduced pressure
  2. washwashed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. dissolutionThe crude product was dissolved in methanol
  7. additiontreated with decolorizing carbon
  8. filtrationfiltered through celite
  9. concentrationconcentrated
  10. customThe resultant solid was recrystallized from toluene

Sources & evidence

ORD record
ord-1a91c10e2bb44e68bc2cfc613bff343c
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

Loading…