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

HRID 5627

Reaktionsgleichung

Reaktionsgleichung von HRID 5627
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

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)).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1e30286531164f3e818011ff3a8385c4
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245056

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