Trifluoroacetic acid → HCID 67461567, compound

Reaction equation

FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11]([C:13]1[CH:17]=[N:16][N:15](C2CCN(C(OC(C)(C)C)=O)CC2)[N:14]=1)=[O:12])[CH3:9].C(OC(C1N([CH:41]2[CH2:46][CH2:45][N:44](C(OC(C)(C)C)=O)[CH2:43][CH2:42]2)N=NC=1)=O)C>>[N:44]1([C:13]2([C:11]([O:10][CH2:8][CH3:9])=[O:12])[CH:17]=[N:16][NH:15][NH:14]2)[CH2:45][CH2:46][CH2:41][CH2:42][CH2:43]1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 67462532HCID 67462532, compound

HCID 67462944HCID 67462944, compound

Product 1

HCID 67461567HCID 67461567, compound

Procedure

Trifluoroacetic acid (3 mL) was added to 1,1-dimethylethyl 4-[4-(ethoxycarbonyl)-2H-1,2,3-triazol-2-yl]-1-piperidinecarboxylate (0.41 g, 1.3 mmol) (i.e. the product of Example 32, Step A). The reaction mixture was stirred for 45 minutes. The reaction mixture was then concentrated in vacuo. The resulting mixture was treated with saturated aqueous sodium bicarbonate and the aqueous layer was extracted three times with dichloromethane. The solvent was removed with a rotary evaporator to afford 0.23 g of ethyl 4-piperidinyl-2H-1,2,3-triazole-4-carboxylate as an oil. This compound was of sufficient purity to use in subsequent reactions.