Acetone → disodium heptadecanoyl-L-aspartate

HRID 848938

반응식

HRID 848938 반응식
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+:11].CC(C)=O.[C:16](Cl)(=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>O>[C:16]([NH:1][C@H:2]([C:7]([O-:9])=[O:8])[CH2:3][C:4]([O-:6])=[O:5])(=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[Na+:11].[Na+:11]

참가 물질

6

반응물 4

HCID 180AcetoneHCID 5960L-Aspartic Acid2회HCID 14798Sodium Hydroxide2회HCID 3516438Heptadecanoyl Chloride

생성물 1

HCID 86755011disodium heptadecanoyl-L-aspartate

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
0 °C

실험 절차

In a one L three-necked flask were placed 16.0 g (0.12 mol) of L-aspartic acid and an aqueous solution of 9.6 g (0.24 mol) of sodium hydroxide in 150 mL of water under stirring. After the L-aspartic acid was dissolved, 120 mL of acetone was added to the mixture in the flask. Then, to the resultant reaction liquid which had been cooled to 0° C. were added dropwise over a period of 30 minutes, 29.0 g (0.1 mol) of heptadecanoyl chloride and an aqueous solution of 4 g sodium hydroxide in 30 mL of water, while maintaining the reaction temperature at 0 to 5° C. and pH at 11 to 12. Thereafter, by gradually raising the temperature of the reaction liquid to room temperature (25° C.) under stirring over a period of 2 hours, a solution of disodium heptadecanoyl-L-aspartate was obtained. To the resultant solution was added 65 mL of 5N hydrochloric acid to lower the pH of the solution to 1. The crystal thus precipitated was separated from the solution by means of vacuum filtration, washed with water and dried under reduced pressure. The resultant crystal was washed with 500 mL of hexane, dried and recrystallized from a mixed solvent of ethanol/water (8:1). As a result 21.0 g (0.054 mol) of N-heptadecanoyl-L-aspartic acid was obtained in a yield of 54.3% based on the fed heptadecanoyl chloride. The physical properties of the objective N-heptadecanoyl-L-aspartic acid were as follows.

후처리

  1. customThen, to the resultant reaction liquid which
  2. additionwere added dropwise over a period of 30 minutes
  3. temperatureThereafter, by gradually raising
  4. customthe temperature of the reaction liquid to room temperature (25° C.)

출처 및 근거

ORD 기록
ord-6cd7d4bb31cc4b66b432d38bbedef8d1
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06010708

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