Ethyl Acetate → HCID 58866146, compound

HRID 1354274Notes

Reaction equation

HRID 1354274 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C@@H:12]1[N:17]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:16][C@@H:15]2[O:29][C:30]([CH3:33])([CH3:32])[O:31][C@@H:14]2[C@H:13]1[O:34]C(=O)C)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].C(OCC)(=O)C>CO>[CH2:1]([O:8][NH:9][C:10]([C@@H:12]1[N:17]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:16][C@@H:15]2[O:29][C:30]([CH3:32])([CH3:33])[O:31][C@H:14]2[C@H:13]1[OH:34])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10942334Sodium Methoxide2×HCID 86598882HCID 86598882, compound

Product 1

HCID 58866146HCID 58866146, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above compound (4) (1.85 g) was dissolved in methanol (25 mL) and 28% NaOMe (668 mg) was added, and then the mixture was stirred at room temperature for 2 hours. Furthermore, 28% NaOMe (334 mg) was added and, after stirring at room temperature for 3 hours, the reaction solution was mixed with ethyl acetate (150 mL) and then washed with 0.5N hydrochloric acid and saturated saline. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure, and then the resulting residue was purified by silica gel medium pressure column chromatography (ethyl acetate:cyclohexane=2:3) to obtain the titled compound (1.36 g) as a syrup.

Workup

  1. stirringafter stirring at room temperature for 3 hours
  2. washwashed with 0.5N hydrochloric acid and saturated saline
  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=2:3)

Sources & evidence

ORD record
ord-3eb5234d5913483980593d5a3de9fc5d
Source dataset
uspto-grants-2007_05
Patent number
US07223779B2

Reaction notes

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