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3,4-dihydro-2H-pyran → rac-(2RS,3RS,5SR)-5-benzyloxy-2-hexyl-3-hydroxy-decanoic acid

HRID 5627
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HRID 5627 반응식
[CH2:1]([CH:7]1[CH:13]([OH:14])[CH2:12][CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]CCCCCC)[O:10][C:8]1=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O1C=CC[CH2:28][CH2:27]1.[NH+]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[OH-:38].[Na+]>CC(OC)(C)C>[CH2:33]([O:10][CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH:13]([OH:14])[CH:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]([OH:9])=[O:38])[C:34]1[CH:28]=[CH:27][CH:37]=[CH:36][CH:35]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 80803,4-dihydro-2H-pyranHCID 14798Sodium HydroxideHCID 4989215PyridiniumHCID 106658573-Hexyl-4-hydroxy-6-undecyl-tetrahydropyran-2-one

생성물 1

HCID 20084763rac-(2RS,3RS,5SR)-5-benzyloxy-2-hexyl-3-hydroxy-decanoic acid

시약·촉매·용매 1

HCID 15413
tert-Butyl methyl ether
용매

실험 절차

177.3 mg of rac-(2RS,3RS,5SR)-2-hexyl-3-hydroxy-5-undecyl-δ-valerolactone (Example 1c)), 750 ml of TBME, 86.7 g of 97% 3,4-dihydro-2H-pyran and 0.314 g of pyridinium p-toluenesulphone were stirred at 50° under argon for 20 hours. 500 ml of 2N sodium hydroxide solution were added to the reaction solution. After stirring at 50° for 2.5 hours the aqueous phase was separated and the organic phase was washed with 500 ml of 10% sodium chloride solution. salt slurry was cooled, treated under argon in succession with 152.7 g of benzyl bromide and 99.1 g of Na t-butylate and stirred at room temperature for 24 hours. After adding 750 ml of 2N hydrochloric acid and stirring at 50° for 22 hours the mixture was cooled, the aqueous phase was separated and the organic phase was washed with sodium chloride solution, dried and filtered. After evaporation of the solvent there were obtained 349.8 g of rac-(2RS,3RS,5SR)-5-benzyloxy-2-hexyl-3-hydroxy-decanoic acid (the product of Examples 1g and 12c)).

후처리

  1. customwas separated
  2. washthe organic phase was washed with 500 ml of 10% sodium chloride solution
  3. temperaturesalt slurry was cooled
  4. additiontreated under argon in succession with 152.7 g of benzyl bromide and 99.1 g of Na t-butylate
  5. stirringstirred at room temperature for 24 hours
  6. additionAfter adding 750 ml of 2N hydrochloric acid
  7. stirringstirring at 50° for 22 hours the mixture
  8. temperaturewas cooled
  9. customthe aqueous phase was separated
  10. washthe organic phase was washed with sodium chloride solution
  11. customdried
  12. filtrationfiltered
  13. customAfter evaporation of the solvent there

출처 및 근거

ORD 기록
ord-1e30286531164f3e818011ff3a8385c4
출처 데이터셋
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05245056

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