Hydrochloric Acid → Hydrochloric Acid

HRID 713192Notes

Reaction equation

HRID 713192 reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[S:9]([CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)(=[O:11])=[O:10].[CH3:25][O-:26].[Na+].[ClH:28]>CO.O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([O:26][CH3:25])[CH:5]=[CH:4][C:3]=1[S:9]([CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1)(=[O:10])=[O:11].[ClH:28]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 96845502HCID 96845502, compound

Product 2

HCID 313Hydrochloric AcidYield 1,132.8%HCID 118159230HCID 118159230, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of tert-butyl 4-((2,4-difluorophenyl)sulfonyl)piperidine-1-carboxylate (50 mg, 0.138 mmol) in MeOH (461 μL) was added sodium methoxide (25.6 μL, 0.138 mmol, 5.4 M in MeOH) dropwise. The reaction mixture was allowed to stir at 45° C. for 20 min then concentrated in vacuo. Boc deprotection was carried out by addition of HCl (138 μL, 0.553 mmol, 4 M in dioxane) to the crude reaction mixture in 300 μL dioxane. Stirring at 50° C. for 24 h followed by concentration in vacuo yielded the title compound as its HCl salt (57 mg) as a white solid (10:1 regioisomeric mixture). ESI-MS m/z [M+H]+274.00.

Workup

  1. concentrationthen concentrated in vacuo
  2. stirringStirring at 50° C. for 24 h
  3. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-c3570d5e9d9d47c2aefff6e2fd4425f9
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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