StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Trimethyl orthoacetate → HCID 57965495, Verbindung

HRID 1695552
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1695552
CC1C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.C[O:19][C:20](OC)(OC)[CH3:21].[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:41]3[CH:40]=[C:39]4[CH2:42][CH2:43][C@@H:44]5[C@@H:49]([C@@:38]4([CH3:60])[CH2:37][C:36]=3[CH:35]=[N:34]2)[C@@H:48]([OH:50])[CH2:47][C@:46]2([CH3:59])[C@:51]([C:55](=[O:58])[CH2:56][OH:57])([OH:54])[CH2:52][CH2:53][C@@H:45]52)=[CH:29][CH:28]=1.O.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.O.CCOC(C)=O>[C:20]([O:54][C@@:51]1([C:55](=[O:58])[CH2:56][OH:57])[C@:46]2([CH3:59])[C@H:45]([C@H:44]3[C@H:49]([C@@H:48]([OH:50])[CH2:47]2)[C@@:38]2([CH3:60])[CH2:37][C:36]4[CH:35]=[N:34][N:33]([C:30]5[CH:29]=[CH:28][C:27]([F:26])=[CH:32][CH:31]=5)[C:41]=4[CH:40]=[C:39]2[CH2:42][CH2:43]3)[CH2:53][CH2:52]1)(=[O:19])[CH3:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 15050Trimethyl orthoacetateHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 117335461-[(1S,2R,13S,14S,17R,18S,20S)-7-(4-fluorophenyl)-17,20-dihydroxy-2,18-dimethyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-yl]-2-hydroxyethanone

Produkt 1

HCID 57965495HCID 57965495, VerbindungAusbeute 16,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

According to the literature (Chem. Pharm. Bull. 2006, 54(11), 1567-1570) pyridine 4-methylbenzenesulfonate (0.034 g, 0.14 mmol) and 1,1,1-trimethoxyethane (0.136 ml, 1.06 mmol) were added to a solution of 1-[(1R,3aS,3bS,10aR,10bS,11S,12aS)-7-(4-fluorophenyl)-1,11-dihydroxy-10a,12a-dimethyl-1,2,3,3a,3b,4,5,7,10,10a,10b,11,12,12a-tetradecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-yl]-2-hydroxyethanone (Steroids 2003 (68) 177-191) (0.34 g, 0.71 mmol) in DCM (15 ml). The mixture was stirred at room temperature for 4 hours, concentrated under reduced pressure, the obtained residue was dissolved in acetone (10 ml) and 4-methyl benzenesulfonic acid hydrate (0.21 g, 1.10 mmol) dissolved in water (10 ml) was added while cooling in an ice-bath. The mixture was stirred for 60 min. at the same temperature followed by the addition of sat. NaHCO3 solution (15 ml) and subsequent extraction with EtOAc (30 ml). The organic layer was washed with brine, dried and purified on a preparative HPLC column (CH3CN/water) and the product containing fractions were freeze-dried to give 60 mg of the title compound.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in acetone (10 ml)
  3. additionwas added
  4. temperaturewhile cooling in an ice-bath
  5. stirringThe mixture was stirred for 60 min. at the same temperature
  6. washThe organic layer was washed with brine
  7. customdried
  8. custompurified on a preparative HPLC column (CH3CN/water)
  9. additionthe product containing fractions
  10. customwere freeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-3be0987c9d9b4b048cd7e31a68fe65ae
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163724B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion