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 2194367Notes

Reaction equation

HRID 2194367 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-7395411dcf764dd3a7c62c5debda2b77
Source dataset
uspto-grants-2012_12
Patent number
US08334279B2

Reaction notes

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