Triethylamine → HCID 14673937, compound

HRID 2372029Notes

Reaction equation

HRID 2372029 reaction equation
[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH2:15])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3.C(N(CC)CC)C.[C:25](Cl)(=[O:28])[CH2:26][CH3:27]>C(Cl)Cl>[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH:15][C:25](=[O:28])[CH2:26][CH3:27])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Product 1

HCID 14673937HCID 14673937, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.29 g (5.48 mmol) of (+)-7,8-dihydro-6,6-dimethyl-7-hydroxy- 8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole [compound (+)I], 690 mg (6.8 mmol) of triethylamine and 40 ml of methylene chloride were stirred at room temperature while 610 mg (6.6 mmol) of propionyl chloride was added thereto. The mixture was stirred at room temperature for four hours. The reaction mixture was extracted with 600 ml of ethyl acetate and 300 ml of water. The organic phase was collected and dried over anhydrous sodium sulfate. The filtrate and the residue obtained after distilling off the solvent were crystallized from a solvent mixture comprising 10 g of ethyl acetate and 5 g of hexane, allowed to stand in a refrigerator overnight and then filtered by means of suction. The obtained crystals were washed with 3-ml portions of ethyl acetate/hexane (2 1) twice and dried under reduced pressure to thereby give the titled compound in the form of a colorless product.

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted with 600 ml of ethyl acetate and 300 ml of water
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe filtrate and the residue obtained
  6. distillationafter distilling off the solvent
  7. customwere crystallized from a solvent mixture
  8. customto stand in a refrigerator overnight
  9. filtrationfiltered by means of suction
  10. washThe obtained crystals were washed with 3-ml portions of ethyl acetate/hexane (2 1) twice
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-5c99ac86d73a433facae820b71fd1324
Source dataset
uspto-grants-1992_03
Patent number
US05097037

Reaction notes

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