Acetic Anhydride → HCID 19884847, compound

HRID 846230Notes

Reaction equation

HRID 846230 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:25])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].[O:32]1C=CC[CH2:34][CH2:33]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC(=O)C)(=O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:25])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[O:31][C:33](=[O:32])[CH3:34])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 19884748HCID 19884748, compound

Product 1

HCID 19884847HCID 19884847, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of the compound of Example 6, (1.2 g, 2.7 mmoles) and dihydropyran (0.8 ml, 4.4 mmoles) in methylene chloride (20 ml) was added p-toluenesulfonic acid monohydrate (5 mg) The reaction mixture was stirred at room temperature for two hours. The solution was cooled to 0° and triethylamine (6 ml), 4-dimethylaminopyridine (DMAP) (15 mg) and acetic anhydride (5 ml) were added. The resulting solution stirred at room temperature for two hours. The solution was washed with 5% NaHCO3 (2×), water, 1N HCl and concentrated in vacuo. The residue was dissolved in THF (6 ml) and stirred with 1N HCl (1 ml) at room temperature for one hour. Dichloromethane (50 ml) and water (50 ml) were added to the solution and the organic layer was collected, washed with brine (4×) dried (Na2SO4) and concentrated in vacuo. The crystalline residue was washed with hexane and recrystallized to afford the title compound, m.p. 121°-123°.

Workup

  1. temperatureThe solution was cooled to 0°
  2. stirringThe resulting solution stirred at room temperature for two hours
  3. washThe solution was washed with 5% NaHCO3 (2×), water, 1N HCl
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in THF (6 ml)
  6. stirringstirred with 1N HCl (1 ml) at room temperature for one hour
  7. additionDichloromethane (50 ml) and water (50 ml) were added to the solution
  8. customthe organic layer was collected
  9. washwashed with brine (4×)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. washThe crystalline residue was washed with hexane
  13. customrecrystallized

Sources & evidence

ORD record
ord-6db0924c91d34c96a184d14171841ed6
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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