Trifluoroacetic acid → HCID 59909835, compound

HRID 2183042Notes

Reaction equation

HRID 2183042 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([C:24]([N:26]([CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[CH3:27])=[O:25])[N:20]=2)[CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([C:24]([N:26]([CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[CH3:27])=[O:25])[N:20]=2)[CH2:11][C:12]([OH:14])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59909840HCID 59909840, compound

Product 1

HCID 59909835HCID 59909835, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (3R)-6-cyclohexyl-3-(3-{[[2-(dimethylamino)ethyl](methyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoate (Preparation 81) (630 mg, 1.40 mmol) in dichloromethane (5 ml) was treated with trifluoroacetic acid (5 ml) and stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the residue azeotroped from dichloromethane. The residue was purified by column chromatography on silica gel eluting with a gradient system of 100:0 (dichloromethane:methanol) gradually changing to 90:10 (dichloromethane:methanol) to afford the title compound as a colourless gum (453 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from dichloromethane
  3. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of 100:0 (dichloromethane:methanol)

Sources & evidence

ORD record
ord-9af6bccdcef44073bcb1360341d0e121
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

Loading…