Ethyl Acetate → HCID 58866169, compound

HRID 1354286Notes

Reaction equation

HRID 1354286 reaction equation
[CH2:1]([O:8][C:9]([C@H:11]1[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([OH:19])[CH2:13][N:12]1[S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:32]1(C)[CH:37]=CC(S(O)(=O)=O)=C[CH:33]=1.C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:8][C:9]([C@H:11]1[C@@H:16]2[O:17][C:32]([CH3:37])([CH3:33])[O:18][C@@H:15]2[C@@H:14]([OH:19])[CH2:13][N:12]1[S:20]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)(=[O:22])=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 58866182HCID 58866182, compound

Product 1

HCID 58866169HCID 58866169, compoundYield 3,585%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The above compound (4) (7.4 g) was dissolved in DMF (80 mL) and DMP (17.6 g) and p-toluenesulfonic acid monohydrate (70 mg) were added, and then the mixture was stirred overnight at room temperature and further stirred at 60° C. for 1.5 hours. To the reaction solution was added ethyl acetate (150 mL) and, after washing with an aqueous saturated sodium hydrogencarbonate solution and saturated saline (×3), the organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel medium pressure column chromatography (ethyl acetate:cyclohexane=1:3→1:2→1:1) to obtain the titled compound (6.3 g) as a syrup.

Workup

  1. stirringfurther stirred at 60° C. for 1.5 hours
  2. washafter washing with an aqueous saturated sodium hydrogencarbonate solution and saturated saline (×3)
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel medium pressure column chromatography (ethyl acetate:cyclohexane=1:3→1:2→1:1)

Sources & evidence

ORD record
ord-8045ede264134304b4a2cb7714c93c05
Source dataset
uspto-grants-2007_05
Patent number
US07223779B2

Reaction notes

Loading…