Ammonium Chloride → 2-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-[(1E)-3-oxo-4-phenoxy-1-buten-1-yl]-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

HRID 573527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573527
COP([CH2:7][C:8](=[O:17])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)OC.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:26]([C@@H:28]1[C@@H:37]2[C@@H:31]([O:32][CH2:33][C@@H:34]([CH2:38][CH2:39][CH2:40][C:41]([O:43][CH:44]([CH3:46])[CH3:45])=[O:42])[CH2:35][CH2:36]2)[CH2:30][C@H:29]1[O:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][O:49]1)=O.[Cl-].[NH4+]>C1COCC1>[O:17]=[C:8]([CH2:9][O:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)/[CH:7]=[CH:26]/[C@@H:28]1[C@@H:37]2[C@@H:31]([O:32][CH2:33][C@@H:34]([CH2:38][CH2:39][CH2:40][C:41]([O:43][CH:44]([CH3:45])[CH3:46])=[O:42])[CH2:35][CH2:36]2)[CH2:30][C@H:29]1[O:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][O:49]1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 580104Dimethyl 2-oxo-3-phenoxypropylphosphonateHCID 866653202-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-formyl-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

Produkt 1

HCID 687522552-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-[(1E)-3-oxo-4-phenoxy-1-buten-1-yl]-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoateAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under the argon atmosphere, dimethyl-(3-phenoxy-2-oxopropyl)-phosphonate (826 mg, 3.20 mmol) and potassium phosphate (679 mg, 3.20 mmol) were added to a THF solution (16 mL) of the compound (634 mg, 1.60 mmol) produced in Example 13, followed by stirring at room temperature for one day. The reaction solution was added to an aqueous saturated ammonium chloride solution, and the aqueous layer was extracted with ethyl acetate twice. The collected organic layers were washed with a saturated saline, and dried with anhydrous sodium sulfate. The solution was concentrated under reduced pressure, and purified with a column apparatus (Hiflash-SI, Size L, hexane→ethyl acetate:hexane=4:6) manufactured by Yamazen Corporation to obtain a titled compound (426 mg) having the following physical property values.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with ethyl acetate twice
  2. washThe collected organic layers were washed with a saturated saline
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationThe solution was concentrated under reduced pressure
  5. custompurified with a column apparatus (Hiflash-SI, Size L, hexane→ethyl acetate:hexane=4:6)

Quellen und Nachweise

ORD-Eintrag
ord-6b2f62418dda4625be0ff997bdda2361
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029574B2

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