Acetyl chloride → (S)-N-(1-(5-Hydroxypyridin-2-yl)ethyl)acetamide

HRID 40575Notes

Reaction equation

HRID 40575 reaction equation
[NH2:1][C@H:2]([C:4]1[N:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:3].[C:11](Cl)(=[O:13])[CH3:12]>C1COCC1>[OH:10][C:7]1[CH:6]=[CH:5][C:4]([C@@H:2]([NH:1][C:11](=[O:13])[CH3:12])[CH3:3])=[N:9][CH:8]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 78960964HCID 78960964, compound

Product 1

HCID 86687917(S)-N-(1-(5-Hydroxypyridin-2-yl)ethyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1.00 g (5.73 mmol) (S)-6-(1-aminoethyl)pyridin-3-ol in 10 ml THF and 3.99 mL TEA (28.6 mmol) are slowly added 494 mg (6.30 mmol) acetyl chloride and stirring is continued for 2 h. The reaction is quenched by the addition of water and extracted several times with DCM. The org. layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, DCM/MeOH/NH3 90/9/1).

Workup

  1. customThe reaction is quenched by the addition of water
  2. extractionextracted several times with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo
  6. customThe crude product is purified by column chromatography (silica gel, DCM/MeOH/NH3 90/9/1)

Sources & evidence

ORD record
ord-e05a20423a9346b1b6c342b34195757b
Source dataset
uspto-grants-2013_09
Patent number
US08530460B2

Reaction notes

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