Water → HCID 70267654, compound

HRID 2289372Notes

Reaction equation

HRID 2289372 reaction equation
[OH-:1].[K+].O.[O:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[O:10][C@H:11]([CH2:15][C@@H:16]([CH3:21])[CH2:17][CH2:18][CH2:19][CH3:20])[C:12](N)=[O:13]>C(O)C>[O:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[O:10][C@H:11]([CH2:15][C@@H:16]([CH3:21])[CH2:17][CH2:18][CH2:19][CH3:20])[C:12]([OH:1])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 70270372HCID 70270372, compound

Product 1

HCID 70267654HCID 70267654, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In an egg-plant type flask were charged 7.66 g of 85% potassium hydroxide, 3 ml of water, 60 ml of ethanol, and 3.0 g of the compound obtained in Step 6, and the mixture was refluxed for 10 hours. Ethanol was removed by distillation under reduced pressure, and 30 ml of water was added to the residue. The mixture was adjusted to pH 1 with concentrated hydrochloric acid and then extracted with ethyl acetate. The extract was washed with water, and the solvent was removed by distillation under reduced pressure to obtain 2.6 g of a crude product. Purification by silica gel column chromatography gave 1.8 g (59.77%) of the titled compound.

Workup

  1. temperaturethe mixture was refluxed for 10 hours
  2. customEthanol was removed by distillation under reduced pressure, and 30 ml of water
  3. additionwas added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customthe solvent was removed by distillation under reduced pressure
  7. customto obtain 2.6 g of a crude product
  8. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-befa043881be4da5b8c273d5c95fe733
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

Loading…