Hydrochloric Acid → Retinoyl beta-glucuronide

HRID 1722493노트

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HRID 1722493 반응식
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18](F)=[O:19].[O:23]=[CH:24][C@@H:25]([C@H:27]([C@@H:29]([C@@H:31]([C:33]([OH:35])=[O:34])[OH:32])[OH:30])[OH:28])[OH:26].C(=O)(O)[O-].[Na+].Cl>CC(C)=O.O>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18]([O:23][C@@H:24]1[O:32][C@H:31]([C:33]([OH:35])=[O:34])[C@@H:29]([OH:30])[C@H:27]([OH:28])[C@H:25]1[OH:26])=[O:19]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 65041Glucuronic AcidHCID 516892Sodium BicarbonateHCID 5378594(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl fluoride3회

생성물 1

HCID 5281877Retinoyl beta-glucuronide수율 60%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매4회

실험 절차

Retinoyl fluoride (2.4 g) was dissolved in 300 ml of acetone. D-Glucuronic acid (6 g) dissolved in 75 ml of water and sodium bicarbonate (6 g) dissolved in 75 ml of water were added to the retinoyl fluoride solution. The mixture was stirred at room temp. for 12-16 hours. More water (100-150 ml) was added and the stirring was continued for 8-12 hours more until most of the retinoyl fluoride had reacted. The solution was diluted with water, acidified with 1N HCl, and the product was extracted with n-butanol. The extract was washed with water, dried over anhydrous sodium sulfate and then evaporated to dryness in a rotary evaporator. The residue was dissolved in 2-3 ml of diethyl ether and transferred to a silica gel (for dry column chromatography, wet packed with hexane) column. The column was developed with hexane containing diethyl ether (5-50%) to remove retinoic acid and other products. The major yellow band containing retinoyl glucuronide was next eluted with a mixture of CH2Cl2 /CH3OH (1:1). The solvent was evaporated to dryness to give solid retinoyl glucuronide (2.1 g, 60%).

후처리

  1. waitthe stirring was continued for 8-12 hours
  2. extractionthe product was extracted with n-butanol
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness in a rotary evaporator
  6. dissolutionThe residue was dissolved in 2-3 ml of diethyl ether
  7. additioncontaining diethyl ether (5-50%)
  8. customto remove retinoic acid and other products
  9. additionThe major yellow band containing retinoyl glucuronide
  10. washwas next eluted with a mixture of CH2Cl2 /CH3OH (1:1)
  11. customThe solvent was evaporated to dryness

출처 및 근거

ORD 기록
ord-8aee466b86754c8289dea6d847fc67a7
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04855463

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