Reaktion #86294

ord-1257f732a9eb4aaaa261c893da57fb5b

Reaktionsgleichung

CC(=O)OCC(O[Si](C)(C)C)=C1[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3=CC[C@]12C
crude product
CC(=O)OCC(O[Si](C)(C)C)=C1[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3=CC[C@]12C
2-((10S,13S,16R)-10,13,16-trimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-(trimethylsilyloxy)ethyl acetate
Cl
HCl
O=C([O-])O.[K+]
potassium bicarbonate
→
CC(=O)OCC(=O)[C@H]1[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3=CC[C@@]21C
2-oxo-2-((10S,13S,16R,17S)-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)ethyl acetate

Edukte

CC(=O)OCC(O[Si](C)(C)C)=C1[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3=CC[C@]12C
crude product
CC(=O)OCC(O[Si](C)(C)C)=C1[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3=CC[C@]12C
2-((10S,13S,16R)-10,13,16-trimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-(trimethylsilyloxy)ethyl acetate
Cl
HCl
O=C([O-])O.[K+]
potassium bicarbonate

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
ethyl acetate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Trocknenthe ethyl acetate phase is dried
  2. 2
    Filtrationfiltered
  3. 3
    Einengenconcentrated to a semi-solid

Vorschrift

The crude product from step 1 is dissolved in ethyl acetate, and slurried with aqueous 1N HCl until hydrolysis is complete. The aqueous acid is neutralized with aqueous potassium bicarbonate, and the ethyl acetate phase is dried, filtered, and concentrated to a semi-solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434758B2uspto-grants-2016_09