Trifluoroacetic acid → HCID 67461567, compound

HRID 2043785Notes

Reaction equation

HRID 2043785 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

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67462532HCID 67462532, compoundHCID 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.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionThe resulting mixture was treated with saturated aqueous sodium bicarbonate
  3. extractionthe aqueous layer was extracted three times with dichloromethane
  4. customThe solvent was removed with a rotary evaporator

Sources & evidence

ORD record
ord-98c55d7d55f1405d8b3e1862e43c6597
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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