Hydrochloric Acid → Retinoyl beta-glucuronide

HRID 346217

반응식

HRID 346217 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 fluoride2회

생성물 1

HCID 5281877Retinoyl beta-glucuronide수율 61.1%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매3회

실험 절차

Retinoyl fluoride (2.4 g, 7.9 mmol) was dissolved in 200 ml of acetone. D-glucuronic acid (6 g, 31 mmol) dissolved in 50 ml of water and sodium bicarbonate (970 mg) dissolved in 50 ml of water were added to the retinoyl fluoride solution. The mixture was stirred at room temperature for 20-24 hrs. The solution was neutralized with 1N HCl, diluted with water, and the product was extracted with ethyl acetate. 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 β-glucuronide (2.3 g, 60%). This preparation consisted mainly of the all-trans isomer, and can be used as such.

후처리

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

출처 및 근거

ORD 기록
ord-f6f720e4f99c4eca8d42709384fb9f64
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05061723

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