Methanol → HCID 22463679, compound

HRID 1935295Notes

Reaction equation

HRID 1935295 reaction equation
[C:1]([N:16]([CH3:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[OH-].[Na+].[CH3:25]O>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:25][O:20][C:19](=[O:21])[CH2:18][CH2:17][N:16]([C:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18427123Myristoyl methyl beta-alanine

Product 1

HCID 22463679HCID 22463679, compound

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

313 g of N-myristoyl-N-methyl-β-alanine (manufactured by Kawaken Fine Chemical Co.) and 256 g of methanol were put into a 1000 ml flask, to which was added 2.85 g of p-toluenesulfonic acid as catalyst, and the mixture was heated for reaction under reflux for 5 hours. After its acid value was confirmed to be not larger than 10, the reaction mixture was neutralized with 1.2 g of an aqueous solution of sodium hydroxide (50%), and then the methanol was evaporated away under reduced pressure. The resulting residue was washed with water and dried to obtain N-myristoyl-N-methyl-β-alanine methyl ester. A 163 g portion of this N-myristoyl-N-methyl-β-alanine methyl ester and 379 g of decaglycerin (manufactured by Sakamoto Pharmaceutical Industry Co.), and then 1.1 g of sodium hydroxide were put into a 1000 ml flask, the atmosphere of which was then replaced with nitrogen. Then, the mixture was subjected to transesterification reaction by keeping it at 150° C. and not more than 60 mmHg for 6 hours to obtain 460 g of a pasty or oily product.

Workup

  1. temperaturethe mixture was heated for reaction
  2. temperatureunder reflux for 5 hours
  3. customthe methanol was evaporated away under reduced pressure
  4. washThe resulting residue was washed with water
  5. customdried

Sources & evidence

ORD record
ord-21da84f0b9244e6796dc46e41e4a7206
Source dataset
uspto-grants-2002_05
Patent number
US06387359B1

Reaction notes

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