Trifluoroacetic acid → HCID 22872664, compound

HRID 1780368Notes

Reaction equation

HRID 1780368 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([O:16][CH2:17][C@@H:18]2[CH2:21][CH2:20][N:19]2C(OC(C)(C)C)=O)[CH:12]=[N:13][C:14]=1[Cl:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[ClH:15].[C:1]([C:9]1[CH:10]=[C:11]([O:16][CH2:17][C@@H:18]2[CH2:21][CH2:20][NH:19]2)[CH:12]=[N:13][C:14]=1[Cl:15])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22872663HCID 22872663, compound

Product 1

HCID 22872664HCID 22872664, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-benzoyl-6-chloro-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from step 107a is dissolved in methylene chloride (10 mL). The mixture is cooled to 0° C., TFA (10 mL) is added and the reaction is stirred for 45 minutes as it warms to room temperature. The mixture is concentrated in vacuo and taken up in a minimum amount of H2O. The aqueous mixture is basified with 15% NaOH and extracted with CH2Cl2 (200 mL), which is dried (MgSO4) and concentrated. The residue is chromatographed (silica gel) to afford the free amine. The isolated free amine is taken up in a minimum amount of Et2O, cooled to 0° C., and treated with HCl in ethanol to afford the hydrochloride salt.

Workup

  1. customwarms to room temperature
  2. concentrationThe mixture is concentrated in vacuo
  3. extractionextracted with CH2Cl2 (200 mL), which
  4. dry with materialis dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is chromatographed (silica gel)

Sources & evidence

ORD record
ord-b1825b6bbc9c46158398371d2988c944
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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