Trifluoroacetic acid → HCID 89713626, compound

HRID 1518975Notes

Reaction equation

HRID 1518975 reaction equation
[CH3:1][O:2][C@@H:3]1[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][C@H:4]1[C:16]1[S:17][CH:18]=[CH:19][N:20]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C@@H:3]1[CH2:8][CH2:7][NH:6][CH2:5][C@H:4]1[C:16]1[S:17][CH:18]=[CH:19][N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89713521HCID 89713521, compound

Product 1

HCID 89713626HCID 89713626, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir tert-butyl trans-4-methoxy-3-thiazol-2-yl-piperidine-1-carboxylate (4.8 g, 16.1 mmol) in dichloromethane (80.4 mL) and add trifluoroacetic acid (7.30 mL, 96.51 mmol). Stir the mixture at ambient temperature overnight. Remove the solvent under reduced pressure, and purify the residue via SCX (50 g cartridge) eluting with 2N NH3/MeOH. Concentrate the appropriate fractions under reduced pressure to give the title compound (3.2 g, 85.3%) as a waxy solid. MS (m/z): 199 (M+1).

Workup

  1. customRemove the solvent under reduced pressure
  2. custompurify the residue via SCX (50 g cartridge)
  3. washeluting with 2N NH3/MeOH
  4. concentrationConcentrate the appropriate fractions under reduced pressure

Sources & evidence

ORD record
ord-b7afed136fb74d8d861c48893c4bcdf6
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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