Ethyl Acetate → HCID 13754459, compound

HRID 980583Notes

Reaction equation

HRID 980583 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:27])[CH:11]([C:20]1(O)[CH2:25][CH2:24][O: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.C1C=CN=CC=1.O=S(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>N1C=CC=CC=1.O>[CH2:1]([O:8][N:9]1[C:20]2([CH2:25][CH2:24][O: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:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 168533Sulfur trioxide-pyridineHCID 13754454HCID 13754454, compound

Product 1

HCID 13754459HCID 13754459, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Conditions

Temperature
57 °C

Procedure

N-(Benzyloxy)-N2 -(t-butoxycarbonyl)-α-(4-hydroxy-2,3,5,6-tetrahydro-4-pyranyl)glycinamide (1.9 g, 5 mmoles) in 20 ml of dry pyridine under argon was treated with 1.05 g (6.5 mmoles) of pyridine-sulfur trioxide and heated to 57° C. for 2 hours. The volatiles were removed in vacuo. Dry acetonitrile was added and evaporated four times, and the residue was treated with a solution of 5 g (36 mmole) of potassium carbonate in 12.5 ml of water, followed by 40 ml of ethyl acetate. The mixture was heated to reflux with vigorous stirring for 6 hours. The mixture was cooled, diluted with water, and the layers separated. The organics were washed with 3% potassium bisulfate and brine, dried (sodium sulfate) and evaporated to a solid. Chromatography on 350 ml of LPS-1 in hexane:ethyl acetate (1:1) and evaporation of the pure product fractions (Rf=0.56 in same solvent) gave a solid. Trituration with isopropyl ether and air drying gave the product as a white solid, 0.78 g, melting point 144°-146° C.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionDry acetonitrile was added
  3. customevaporated four times
  4. temperatureThe mixture was heated
  5. temperatureto reflux
  6. temperatureThe mixture was cooled
  7. customthe layers separated
  8. washThe organics were washed with 3% potassium bisulfate and brine
  9. dry with materialdried (sodium sulfate)
  10. customevaporated to a solid
  11. customChromatography on 350 ml of LPS-1 in hexane:ethyl acetate (1:1) and evaporation of the pure product fractions (Rf=0.56 in same solvent)
  12. customgave a solid
  13. dry with materialTrituration with isopropyl ether and air drying

Sources & evidence

ORD record
ord-d1ecd8ac25c148c8b69081adf8144647
Source dataset
uspto-grants-1987_01
Patent number
US04638060

Reaction notes

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