Acetic Acid → HCID 53632317, compound

HRID 2232596Notes

Reaction equation

HRID 2232596 reaction equation
[H-].[Na+].BrCC(OC1CCCCO1)[CH2:6][C:7]([NH:9][CH2:10][C:11](OCC)=O)=[O:8].[C:23]([OH:26])(=O)[CH3:24].[C:27]([O:30][CH2:31][CH3:32])(=[O:29])[CH3:28].O1C[CH2:36][CH2:35][CH2:34]1>O>[O:8]=[C:7]1[CH2:6][CH:11]([CH:23]2[CH2:24][CH2:36][CH2:35][CH2:34][O:26]2)[CH2:10][N:9]1[CH2:28][C:27]([O:30][CH2:31][CH3:32])=[O:29]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 21284017HCID 21284017, compound

Product 1

HCID 53632317HCID 53632317, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

150 mg NaH are suspended in 20 ml tetrahydrofuran, and the mixture is cooled in ice. To this suspension is added a solution of 2.5 g ethyl 2-(4-bromo-3-(tetrahydropyran-2-yloxy)butanamido)acetate in 30 ml tetrahydrofuran. The mixture is stirred 40 min, then poured with stirring into a solution of 1 ml acetic acid in 10 ml water at 0° C. The solution is extracted with ether, the organic phase is washed with a saturated solution of NaHCO3, then washed with brine, dried and evaporated. The crude oil obtained is purified by chromatography on silica, eluting with ethyl acetate. A colourless oil is obtained, Rf 0.32 (silica gel plates, thickness 0.25 mm, eluent ethyl acetate).

Workup

  1. temperaturethe mixture is cooled in ice
  2. additionpoured
  3. extractionThe solution is extracted with ether
  4. washthe organic phase is washed with a saturated solution of NaHCO3
  5. washwashed with brine
  6. customdried
  7. customevaporated
  8. customThe crude oil obtained
  9. customis purified by chromatography on silica
  10. washeluting with ethyl acetate
  11. customA colourless oil is obtained

Sources & evidence

ORD record
ord-864c6e3cc7ee4d7396d3eeea788b23e0
Source dataset
uspto-grants-1988_11
Patent number
US04788300

Reaction notes

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