Water → HCID 14552389, compound

HRID 1110778Notes

Reaction equation

HRID 1110778 reaction equation
[CH2:1]([NH:4][C@@H:5]1[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][C@H:6]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:2][CH3:3].[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22].O>C(O)C>[CH2:25]([O:24][C:20](=[O:23])[CH2:21][CH2:22][N:4]([CH2:1][CH2:2][CH3:3])[C@@H:5]1[CH2:14][CH2:13][C:8]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:7][C@H:6]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 8821Ethyl Acrylate3×HCID 14552387HCID 14552387, compound

Product 1

HCID 14552389HCID 14552389, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 8-(propylamino)-trans-1,4-dioxaspiro[4.5]-decane-7-carboxylate (129.6 g, 0.48 mole) was dissolved in ethanol (1500 ml), then ethyl acrylate (479 g, 4.8 mole) was added. The mixture was refluxed overnight, then additional ethyl acrylate (479 g, 4.8 mole) was added. The mixture was refluxed for 24 hours, at which time a third addition of ethyl acrylate (479 g, 0.48 mole) was made, followed by 60 hours of reflux. The mixture was then cooled to room temperature, poured into water, and the hydrogen ion concentration was adjusted to pH 10. The product was extracted with methylene chloride, dried with sodium sulfate and evaporated to give 177.4 g of crude product. This was purified by HPLC to give 102.1 g of the title product (59.8%).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe mixture was refluxed for 24 hours, at which time
  3. temperatureof reflux
  4. concentrationthe hydrogen ion concentration
  5. extractionThe product was extracted with methylene chloride
  6. dry with materialdried with sodium sulfate
  7. customevaporated
  8. customto give 177.4 g of crude product
  9. customThis was purified by HPLC

Sources & evidence

ORD record
ord-49611422efaf4150a833c52acc4ab701
Source dataset
uspto-grants-1990_12
Patent number
US04977160

Reaction notes

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