Reacción #86294

ord-1257f732a9eb4aaaa261c893da57fb5b

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

CCOC(C)=O
ethyl acetate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Secadothe ethyl acetate phase is dried
  2. 2
    Filtraciónfiltered
  3. 3
    Concentraciónconcentrated to a semi-solid

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09434758B2uspto-grants-2016_09