Sodium Bicarbonate → HCID 59556098, compound

HRID 1809854Notes

Reaction equation

HRID 1809854 reaction equation
[OH:1][C:2]1([C:12]2[CH:21]=[CH:20][C:15]([C:16]([NH:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4][CH2:3]1.C([O-])(O)=O.[Na+].C(OCC)(=O)C.CCCCCC>C1COCC1.Cl>[OH:1][C:2]1([C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH:18][CH3:19])=[O:17])=[CH:20][CH:21]=2)[CH2:11][CH2:10][C:5](=[O:6])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226206Ethyl acetate hexaneHCID 59556067HCID 59556067, compound

Product 1

HCID 59556098HCID 59556098, compoundYield 118.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

4-(8-Hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)-N-methylbenzamide (410 mg, 1.4 mmol) was dissolved in the mixture solvent of 7 mL of THF and 7 mL of 1 N HCl aqueous solution at room temperature. The reaction mixture was then stirred at 60° C. for 1 h. The solution was cooled down to room temperature, adjusted to pH 7-8 with saturated NaHCO3 aqueous solution. The organic layer was separated, and the aqueous layer was extracted twice with EA (20 mL×2). The combined organic extracts were dried over MgSO4 and evaporated to give an oil residue. Chromatography on silica gel (flash chromatography grade) with 40% Ethyl acetate-hexane gave 410 mg (90%) of the desired product: 1H NMR (CDCl3) δ 7.78 (2H, d, J=11.2 Hz), 7.51 (2H, d, J=10.9 Hz), 4.10 (H, s), 3.37 (3H, s), 2.79-2.74 (2H, m), 2.63-2.49 (2H, m), 1.95-1.89 (2H, m), 1.67-1.59 (2H, m); MS: 248 (M+1)+.

Workup

  1. temperatureThe solution was cooled down to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with EA (20 mL×2)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customevaporated
  6. customto give an oil residue

Sources & evidence

ORD record
ord-461e5bbd7a9049aab3bfb54f2bf2951e
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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