Hydrochloric Acid → HCID 59278515, compound

HRID 2067986Notes

Reaction equation

HRID 2067986 reaction equation
CC(S([NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH2:19])=[O:18])[CH:12]=1)[CH2:9][CH3:10])=O)(C)C.Cl>CO>[NH2:7][C@H:8]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH2:19])=[O:18])[CH:12]=1)[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59278114HCID 59278114, compound

Product 1

HCID 59278515HCID 59278515, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[(S)-1-(2-Methyl-propane-2-sulfinylamino)-propyl]-pyridine-2-carboxylic acid amide (5.50 g) in methanol (50 mL) was added hydrochloric acid (4 N in dioxane, 4.3 mL, 17.3 mmol) and the mixture was stirred for 2 h. Additional hydrochloric acid (4 N in dioxane, 0.5 mL, 2.0 mmol) was added. The mixture was stirred for another 1.5 h. The mixture was concentrated to remove methanol and then diluted with ethyl acetate (400 mL), washed with sat. sodium bicarbonate solution, The aqueous layer was extracted with ethyl acetate (4×100 mL). the combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give 4-((S)-1-Amino-propyl)-pyridine-2-carboxylic acid amide (3.50 g, 100%)

Workup

  1. stirringThe mixture was stirred for another 1.5 h
  2. concentrationThe mixture was concentrated
  3. customto remove methanol
  4. additiondiluted with ethyl acetate (400 mL)
  5. washwashed with sat. sodium bicarbonate solution
  6. extractionThe aqueous layer was extracted with ethyl acetate (4×100 mL)
  7. washthe combined organic extracts were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2744ef43ad26418f8c153e5b6ab7f0d9
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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