1-Bromooctane → Glyceryl octyl ascorbic acid

HRID 1698289노트

반응식

HRID 1698289 반응식
[CH2:1]([O:6][C:7]1[C@@H:12]([C@H:13]([CH2:15][OH:16])[OH:14])[O:11][C:9](=[O:10])[C:8]=1[OH:17])[CH:2]([CH2:4][OH:5])[OH:3].C(=O)([O-])O.[Na+].[CH2:23](Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CS(C)=O>[CH2:1]([O:6][C:7]1[C@@H:12]([C@H:13]([CH2:15][OH:16])[OH:14])[O:11][C:9](=[O:10])[C:8]=1[O:17][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:2]([CH2:4][OH:5])[OH:3]

참가 물질

5

반응물 3

HCID 81401-BromooctaneHCID 516892Sodium BicarbonateHCID 672677953-Glyceryl ascorbate

생성물 1

HCID 54588053Glyceryl octyl ascorbic acid수율 61.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Under an argon atmosphere, 3-O-glyceryl ascorbic acid (54.1 g) obtained in Example 1 was stirred in DMSO (200 mL), and further, sodium hydrogen carbonate (18.5 g) was added and the mixture was stirred at room temperature for 30 minutes. Thereafter, octyl bromide (63.7 g) was added and the mixture was heated up to 100° C. and stirred for 3 hours, followed by extraction with ethyl acetate. Then, the extracted liquid was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and 131 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:10/3/0.4), and concentration was performed under reduced pressure to obtain 3-O-glyceryl-2-O-octyl ascorbic acid (48.0 g).

후처리

  1. temperaturethe mixture was heated up to 100° C.
  2. stirringstirred for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThen, the extracted liquid was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure, and 131 g of the resultant residue
  6. washElution
  7. concentrationwas performed with chloroform/methanol/water(volume ratio:10/3/0.4), and concentration

출처 및 근거

ORD 기록
ord-bb3b254aa44549898d5e82008234d856
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163939B2

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