Hydrochloric Acid → HCID 58102816, compound

HRID 386753Notes

Reaction equation

HRID 386753 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])C.CC[O-].[Na+].Cl.CCOC(C)=O>CCO.[Cl-].[Na+].O>[O:3]=[C:4]1[CH2:5][N:6]([C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[CH2:7][CH:8]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 2723922Sodium ethoxideHCID 86649727HCID 86649727, compound2×

Product 1

HCID 58102816HCID 58102816, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To the product of Step B, 1-b, (7.06 g, 24.7 mmol) in EtOH (40 mL) was added NaOEt (20.3 mL, 54.4 mmol, 21 wt in EtOH). The reaction was heated to reflux for 3 h and then cooled before the addition of aq HCl (28 mL, 2 M) followed by dilution with EtOAc and brine. The solution was extracted three times with EtOAc and dried (Na2SO4) to afford the title compound, 1-1, which was used without further purification to prepare Intermediate 4. HPLC/MS: 240.1 (M+1); Rt=2.22 min.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 h
  3. extractionThe solution was extracted three times with EtOAc
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-0ed9f2e76d084fe78af41d4df1191134
Source dataset
uspto-grants-2013_02
Patent number
US08372863B2

Reaction notes

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