Dicyclohexylcarbodiimide → (1 S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl hex-5-enoate

HRID 517381

Reaktionsgleichung

Reaktionsgleichung von HRID 517381
[CH2:1]([C@@H:4]1[C@@H:8](/[CH:9]=[CH:10]/[C@@H:11]([O:24][Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C@H:7]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:6][C@@H:5]1[OH:40])[CH:2]=[CH2:3].[C:41](O)(=[O:47])[CH2:42][CH2:43][CH2:44][CH:45]=[CH2:46].C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:41]([O:40][C@H:5]1[CH2:6][C@@H:7]([O:32][Si:33]([C:36]([CH3:37])([CH3:39])[CH3:38])([CH3:35])[CH3:34])[C@H:8](/[CH:9]=[CH:10]/[C@@H:11]([O:24][Si:25]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:30][CH3:31])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C@H:4]1[CH2:1][CH:2]=[CH2:3])(=[O:47])[CH2:42][CH2:43][CH2:44][CH:45]=[CH2:46]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 153085-Hexenoic AcidHCID 131733345(1 S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanol

Produkt 1

HCID 131733346(1 S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl hex-5-enoateAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A 50 ml two-necked round-bottom flask was flame dried and allowed to be cooled under nitrogen. (1S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanol (1 g, 1.66 mmol) in 10 ml of DMF, 0.05 g (0.33 mmol) of DMAP, 0.21 g (1.83 mmol) of 5-hexenoic acid, and 0.41 g (2.00 mmol) of N,N′-dicyclohexylcarbodiimide were added to the reaction flask. The reaction mixture was heated at 40° C. for 24 hours. The reaction was quenched with 10 ml saturated aqueous sodium bicarbonate. The reaction mixture was phase separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solid was filtered off and organic solvent was evaporated off under vacuum. The crude product was purified by chromatography and then concentrated under reduced pressure to provide 1.05 g of the title compound (90.52% yield).

Aufarbeitung

  1. temperatureA 50 ml two-necked round-bottom flask was flame
  2. customdried
  3. temperatureto be cooled under nitrogen
  4. customThe reaction was quenched with 10 ml saturated aqueous sodium bicarbonate
  5. customseparated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe solid was filtered off
  9. customorganic solvent was evaporated off under vacuum
  10. customThe crude product was purified by chromatography
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3ddc97f407314a828f1dbdde4b8c97da
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115109B2

Verknüpfte Notizen

Wird geladen…