Hydrochloric Acid → HCID 86713151, compound

HRID 713631Notes

Reaction equation

HRID 713631 reaction equation
[CH2:1](/[C:3](/[C:11]#[C:12][C:13]1([OH:28])[C:24]([CH3:26])([CH3:25])[CH2:23][C:16]2(OC(C)C(C)[O:17]2)[CH:15]=[C:14]1[CH3:27])=[CH:4]/[C:5]([NH:7][CH2:8][CH2:9][CH3:10])=[O:6])[CH3:2].Cl.O>CC(C)=O>[CH2:1](/[C:3](/[C:11]#[C:12][C:13]1([OH:28])[C:24]([CH3:26])([CH3:25])[CH2:23][C:16](=[O:17])[CH:15]=[C:14]1[CH3:27])=[CH:4]/[C:5]([NH:7][CH2:8][CH2:9][CH3:10])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86713152HCID 86713152, compound

Product 1

HCID 86713151HCID 86713151, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(2Z)-3-Ethyl-5-(8-hydroxy-2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]dec-6-en-8-yl)-N-propylpent-2-en-4-ynamide (280 mg, 0.72 mmol) was dissolved in acetone (4 ml) under argon in a round-bottom flask, and 10% strength hydrochloric acid was added. The resulting reaction solution was stirred at room temperature for 50 minutes, and water was then added. After removing acetone under reduced pressure, the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By final column chromatography purification of the resulting crude product (ethyl acetate/heptane gradient), it was possible to obtain (2Z)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-N-propylpent-2-en-4-ynamide (200 mg, 88% of theory) in the form of a colorless solid. 1H-NMR (400 MHz, CDCl3 δ, ppm) 6.08 (br. t, 1H, NH), 6.00 (s, 1H), 5.87 (s, 1H), 3.54 (br. s, 1H, OH), 3.27 (m, 2H), 2.53 (d, 1H), 2.42 (d, 1H), 2.27 (q, 2H), 2.17 (s, 3H), 1.56 (sext, 2H), 1.22 (s, 3H), 1.13 (s, 3H), 1.11 (t, 3H), 0.93 (t, 3H).

Workup

  1. customThe resulting reaction solution
  2. customAfter removing acetone under reduced pressure
  3. extractionthe aqueous phase was extracted repeatedly with dichloromethane
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customBy final column chromatography purification of the resulting crude product (ethyl acetate/heptane gradient), it

Sources & evidence

ORD record
ord-f61103129f1b4a52bc2cc034deba7314
Source dataset
uspto-grants-2015_11
Patent number
US09185914B2

Reaction notes

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