Hydrochloric Acid → HCID 57656531, compound

HRID 911613Notes

Reaction equation

HRID 911613 reaction equation
Cl.C(OC([NH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20])=[N:15][CH:16]=1)=O)(C)(C)C>O1CCOCC1.ClCCl>[NH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:22])[CH2:18][CH:19]([CH3:20])[CH3:21])=[N:15][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57656624HCID 57656624, compound

Product 1

HCID 57656531HCID 57656531, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4N hydrogen chloride in dioxane (0.5 mL) to a solution of 5-tert-butoxycarbonylaminomethyl-2-(3-methyl-butyryl)-pyridine (60 mg, 0.2 mmol) in anhydrous dichloromethane (2 mL) and stir the solution overnight. Concentrate in vacuo and partition the residue between saturated aqueous NaHCO3 and dichloromethane. Extract the aqueous phase with dichloromethane (2×15 mL) and EtOAc (2×15 mL). Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the title compound (37 mg, 95%) that was used without any further purification.

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition the residue between saturated aqueous NaHCO3 and dichloromethane
  3. extractionExtract the aqueous phase with dichloromethane (2×15 mL) and EtOAc (2×15 mL)
  4. dry with materialDry the combined organic extracts over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-2adeb38a35c74f9f9f9239d5e7ab4e8e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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