Hydrochloric Acid → 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

HRID 58016

Reaction equation

HRID 58016 reaction equation
[C:1]([O:4][CH2:5][C:6](=[C:12]1[C@:28]2([CH3:29])[CH:15]([CH:16]3[C:25](=[CH:26][CH2:27]2)[C@:24]2([CH3:30])[C:19](=[CH:20][C:21](=[O:31])[CH:22]=[CH:23]2)[CH2:18][CH2:17]3)[CH2:14][C@H:13]1[CH3:32])[O:7][Si](C)(C)C)(=[O:3])[CH3:2].Cl.C(=O)(O)[O-].[K+]>C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6](=[O:7])[C@@H:12]1[C@:28]2([CH3:29])[CH:15]([CH:16]3[C:25](=[CH:26][CH2:27]2)[C@:24]2([CH3:30])[C:19](=[CH:20][C:21](=[O:31])[CH:22]=[CH:23]2)[CH2:18][CH2:17]3)[CH2:14][C@H:13]1[CH3:32])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516893Potassium BicarbonateHCID 672831772-((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

Product 1

HCID 592717402-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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. dry with materialthe ethyl acetate phase is dried
  2. filtrationfiltered
  3. concentrationconcentrated to a semi-solid

Sources & evidence

ORD record
ord-1257f732a9eb4aaaa261c893da57fb5b
Source dataset
uspto-grants-2016_09
Patent number
US09434758B2

Linked notes

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