Pyridine 4-methylbenzene-1-sulfonate → (5Z,13E)-(8R,9S,11R,12R,15S,16RS)-9-Chloro-11,15-dihydroxy-16,19-dimethyl-5,13,18-prostatrienoic Acid

HRID 326183

Reaktionsgleichung

Reaktionsgleichung von HRID 326183
[Cl:1][C@H:2]1[CH2:15][C@@H:14]([O:16]C2CCCCO2)[C@H:13](/[CH:23]=[CH:24]/[C@@H:25]([O:33]C2CCCCO2)[CH:26]([CH3:32])[CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[C@H:3]1[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>C(O)C.C(Cl)Cl>[Cl:1][C@H:2]1[CH2:15][C@@H:14]([OH:16])[C@H:13](/[CH:23]=[CH:24]/[C@@H:25]([OH:33])[CH:26]([CH3:32])[CH2:27][CH:28]=[C:29]([CH3:30])[CH3:31])[C@H:3]1[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Komponenten

5

Edukt 2

HCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 67859606(5Z,13E)-(8R,9S,11R,-12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-5,13,18-prostatrienoic acid

Produkt 1

HCID 67859588(5Z,13E)-(8R,9S,11R,12R,15S,16RS)-9-Chloro-11,15-dihydroxy-16,19-dimethyl-5,13,18-prostatrienoic AcidAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 144 mg of (5Z,13E)-(8R,9S,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-5,13,18-prostatrienoic acid in 2 ml of absolute ethanol was combined with 6.4 mg of pyridine p-toluenesulfonate and agitated for 5 days at room temperature under argon. The reaction mixture was then diluted with 100 ml of methylene chloride, washed twice with saturated sodium chloride solution, dried over magnesium sulfate, and evaporated to dryness under vacuum. The residue was purified by column chromatography on silica gel with hexane/50-100% ethyl acetate as the eluent, thus obtaining 42.5 mg of the desired carboxylic acid as a highly viscous oil.

Aufarbeitung

  1. washwashed twice with saturated sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated to dryness under vacuum
  4. customThe residue was purified by column chromatography on silica gel with hexane/50-100% ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-c98d9cf42f884f8caf14e63d9f3ac74f
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04444788

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