Sulfuric Acid → HCID 20033698, compound

HRID 231693Notes

Reaction equation

HRID 231693 reaction equation
S(=O)(=O)(O)O.COCCOC[O:12][CH:13]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:14][CH2:15][S:16]([C:19]1[S:23][C:22]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>O.CO>[OH:12][CH:13]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:14][CH2:15][S:16]([C:19]1[S:23][C:22]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 57081294HCID 57081294, compound

Product 1

HCID 20033698HCID 20033698, compoundYield 105.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of sulfuric acid (76.7 ml) in water (76.7 ml), cooled to 0° C. was added a solution of compound from Step F (5.2 g, 11.5 mmol) in methanol (76.7 ml) and the reaction mixture was stirred at room temperature for 1 hour. Water was added, extracted with ethyl acetate and the organic layers were washed with saturated NaaHCO3 solution and brine. Drying and solvent evaporation gave an oil (4.4 g) and column chromatography (silica gel, 40% ethyl acetate-hexane) gave a solid product (2.3 g, 56%); m.p. 119°-121° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layers were washed with saturated NaaHCO3 solution and brine
  3. customDrying
  4. customsolvent evaporation

Sources & evidence

ORD record
ord-de6af9b37ae14d2288aaf2ed0d8671db
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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