Sodium Bicarbonate → HCID 57474997, compound

HRID 1052000Notes

Reaction equation

HRID 1052000 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:19][CH2:18][C:13]3(OCC[O:14]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O.C1COCC1.O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:19][CH2:18][C:13](=[O:14])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 86695816HCID 86695816, compound

Product 1

HCID 57474997HCID 57474997, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl-4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-benzoate (4.87 g, 17.56 mmol) in 10% aqueous sulfuric acid (50 mL) and THF (50 mL) was stirred at ambient temperature for 72 hours. The reaction mixture was neutralized by cautious addition of NaHCO3 and simultaneously diluting with water. The aqueous mixture was extracted with EtOAc (2×75 mL) and the combined organic extracts were dried (MgSO4), filtered, and concentrated to give the title compound as an off-white, amorphous solid (4.06 g, 99%) which was used without further purification.

Workup

  1. extractionThe aqueous mixture was extracted with EtOAc (2×75 mL)
  2. dry with materialthe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b7b36c786bc741039c490e7a8f60b823
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

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