Hydrochloric Acid → HCID 68872790, compound

HRID 494636Notes

Reaction equation

HRID 494636 reaction equation
[CH:1]1([CH2:4][CH2:5][C:6]2([CH3:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[CH:8]=[C:7]2[O:17]C)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCOCC1.O>[CH:1]1([CH2:4][CH2:5][C:6]2([CH3:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([OH:16])=[CH:8][C:7]2=[O:17])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68872609HCID 68872609, compound

Product 1

HCID 68872790HCID 68872790, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of Example 157C (1.06 g, 4.10 mmol) in dioxane (10 mL) was added 1 N NaOH (10 mL, 10 mmol) and the reaction mixture heated at 95° C. for 16 hours. After cooling the solution to room temperature, the reaction mixture was diluted with 50 mL of water, the pH adjusted to 2.0 with 1N HCl, and the aqueous layer extracted 3 times with ethyl acetate. The combined organic layers were washed with brine and dried over MgSO4. The product was purified by flash chromatography on SiO2 eluting with a 10-25% ethyl acetate/hexane gradient yielding the title compound (0.635 g, 64% yield) as a crystalline solid. 1H NMR (300 MHz, DMSO-d6): δ ppm−0.51 (m, 2H) −0.02 (m, 2H) 0.14 (m, 2H) 0.46 (m, 1H) 1.16 (s, 3H) 5.42 (s, 1H) 7.12 (t, J=7.35 Hz, 1H) 7.34 (m, 2H) 7.64 (d, J=7.35 Hz, 1H). MS (ESI+) m/z=243 (M+H)+.

Workup

  1. temperatureAfter cooling the solution to room temperature
  2. extractionthe aqueous layer extracted 3 times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customThe product was purified by flash chromatography on SiO2 eluting with a 10-25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-001929de909549fa9668ab0c27f5dacf
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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