6-Acetylaminocaproic acid → Methyl 6-acetamidohexanoate

HRID 981597Notes

Reaction equation

HRID 981597 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])(=[O:3])[CH3:2].S(Cl)(Cl)=O.[CH3:17]N.[Cl-].[Na+]>CO>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:17])=[O:11])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 20056-Acetylaminocaproic acidHCID 5234Sodium ChlorideHCID 6329MethylamineHCID 24386Thionyl Chloride

Product 1

HCID 13718774Methyl 6-acetamidohexanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 6-acetamidohexanoate was prepared as a low-melting solid by sequential treatment of 6-acetamido hexanoic acid with thionyl chloride and methanol. Five grams of this compound, (27 mmol) was dissolved in an excess of 40% aqueous methylamine solution, and the resulting mixture was stirred for sixteen hours at room temperature. The reaction mixture was saturated with sodium chloride and extracted several times with chloroform. The organic layer was dried over magnesium sulfate, and the solvent was removed in vauo to yield a crude residue. Recrystallization from THF yielded 4.5 grams (90%) of pure product, melting point 99°-100° C.

Workup

  1. extractionextracted several times with chloroform
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was removed in vauo
  4. customto yield a crude residue

Sources & evidence

ORD record
ord-8231594aa94b4871b2763647c8e04ba0
Source dataset
uspto-grants-1991_02
Patent number
US04992472

Reaction notes

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