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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 1496723
Notes
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Reaction equation

HRID 1496723 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-449508cd9d1747b0822772bfc28baaee
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09198921B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes