HCID 13754453, compound → HCID 13754457, compound

HRID 980575Notes

Reaction equation

HRID 980575 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:26])[CH:11]([C:20]1(O)[CH2:24][CH2:23][CH2:22][CH2:21]1)[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1C=CC=CC=1>[CH2:1]([O:8][N:9]1[C:20]2([CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:11]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:10]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 13754453HCID 13754453, compound

Product 1

HCID 13754457HCID 13754457, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-(benzyloxy)-N2 -(t-butoxycarbonyl)-α-(1-hydroxycyclopentyl)glycinamide (0.82 g, 2.16 mmole) in 15 ml of pyridine under argon was added pyridine-sulfur trioxide complex (0.47 g, 29.5 mmole). The reaction mixture was heated at 50°-55° C. After 1.5 hours, an additional amount (0.150 g, 0.9 mmole) of pyridine-sulfur trioxide complex was added and the reaction was heated for an additional hour. The reaction mixture was then concentrated in vacuo and azeotroped three times with acetonitrile. To this residue was added a cold mixture of potassium carbonate solution (3.32 g/9 ml water) and ethyl acetate (25 ml). The reaction was stirred vigorously and refluxed for two hours at which point tlc indicated that the reaction was near completion. After cooling, the reaction mixture was diluted with water and ethyl acetate and the phases separated. The organic phase was washed with 5% potassium bisulfate solution and brine and dried over anhydrous sodium sulfate. After evaporating to a residue, the crude benzyl ether was chromatographed on LPS-1 (hexane:ethyl acetate, 3:1) to give 550 mg of pure material.

Workup

  1. temperatureThe reaction mixture was heated at 50°-55° C
  2. additionan additional amount (0.150 g, 0.9 mmole) of pyridine-sulfur trioxide complex was added
  3. temperaturethe reaction was heated for an additional hour
  4. concentrationThe reaction mixture was then concentrated in vacuo
  5. customazeotroped three times with acetonitrile
  6. additionTo this residue was added
  7. additiona cold mixture of potassium carbonate solution (3.32 g/9 ml water) and ethyl acetate (25 ml)
  8. temperaturerefluxed for two hours at which point tlc
  9. temperatureAfter cooling
  10. additionthe reaction mixture was diluted with water and ethyl acetate
  11. customthe phases separated
  12. washThe organic phase was washed with 5% potassium bisulfate solution and brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. customAfter evaporating to a residue
  15. customthe crude benzyl ether was chromatographed on LPS-1 (hexane:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-24601846127e4361ae412d87134bd48a
Source dataset
uspto-grants-1987_01
Patent number
US04638060

Reaction notes

Loading…