Ethyl Acetate → ME-3407

HRID 1089754Notes

Reaction equation

HRID 1089754 reaction equation
[CH2:1]([O:5][C:6]([CH2:8][S:9][C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:7])[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:27])C=1.C(OCC)(=O)C>C(Cl)Cl>[CH2:1]([O:5][C:6]([CH2:8][S:9]([C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:27])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 150356882-[(n-Butoxycarbonylmethyl)thio]thiazolo[5,4-b]pyridine

Product 1

HCID 6918179ME-3407Yield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Dissolved in 50 ml of methylene chloride was 18.5 g of the compound obtained in Example 1, and the solution was cooled down to -10° C. 16.2 g of m-chloroperbenzoic acid (with a 70% purity) was added to the solution, which was in turn stirred at that temperature for 40 minutes. Ethyl acetate (600 ml) was added to the solution, which was then washed once with an aqueous solution of sodium thiosulfate, three times with sodium hydrogencarbonate and once with water, dried over magnesium sulfate, and distilled to remove the solvent. The residue was purified by silica gel column chromatography, and eluting with n-hexane-ethyl acetate (5:3 to 3:1) to obtain the title compound (13.4 g).

Workup

  1. washwas then washed once with an aqueous solution of sodium thiosulfate, three times with sodium hydrogencarbonate and once with water
  2. dry with materialdried over magnesium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with n-hexane-ethyl acetate (5:3 to 3:1)

Sources & evidence

ORD record
ord-2aa131be26f949d2ba44165c7e74aa2a
Source dataset
uspto-grants-1992_01
Patent number
US05079255

Reaction notes

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