Methanol → 2-Methoxycarbonylaminohexanoic acid methyl ester

HRID 224952Notes

Reaction equation

HRID 224952 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4](Br)[CH2:5][CH2:6][CH2:7][CH3:8].[O-:11][C:12]#[N:13].[K+].[CH3:15][OH:16]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:10])[CH:4]([NH:13][C:12]([O:16][CH3:15])=[O:11])[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 95578Hexanoic acid, 2-bromo-, methyl esterHCID 11378442Potassium cyanate

Product 1

HCID 536557612-Methoxycarbonylaminohexanoic acid methyl esterYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.63 grams of 2-bromohexanoic acid methyl ester, 8.52 grams of potassium cyanate and 7.85 grams of methanol were heated in 70 ml of dimethylformamide (DMF) at 100° C. for 45 minutes under vigorous stirring. After the cooling off of the reaction mixture the salts were filtered off and the filtrate concentrated in a vacuum. The viscous residue was taken up with 50 ml of acetone and the undissolved material filtered off. Subsequently the acetone was distilled off and the residue fractionated in the high vacuum. There resulted 10.75 grams (75.5%) of 2-methoxycarbonylaminohexanoic acid methyl ester having a boiling point of 78° C./0.007 mbar.

Workup

  1. filtrationAfter the cooling off of the reaction mixture the salts were filtered off
  2. concentrationthe filtrate concentrated in a vacuum
  3. filtrationthe undissolved material filtered off
  4. distillationSubsequently the acetone was distilled off

Sources & evidence

ORD record
ord-e24802aca7804039894ced150709acc9
Source dataset
uspto-grants-1980_11
Patent number
US04234744

Reaction notes

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