Sulfuric Acid → HCID 67246534, compound

HRID 1027582Notes

Reaction equation

HRID 1027582 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2([CH3:37])[O:18][N:17]=[C:16]([C:19]3[CH:35]=[CH:34][C:22]([C:23]([NH:25][CH2:26][CH:27]4[CH2:31][O:30]C(C)(C)[O:28]4)=[O:24])=[C:21]([CH3:36])[CH:20]=3)[CH2:15]2)[CH:10]=[C:11]([Cl:13])[CH:12]=1>CO>[Cl:13][C:11]1[CH:10]=[C:9]([C:14]2([CH3:37])[O:18][N:17]=[C:16]([C:19]3[CH:35]=[CH:34][C:22]([C:23]([NH:25][CH2:26][CH:27]([OH:28])[CH2:31][OH:30])=[O:24])=[C:21]([CH3:36])[CH:20]=3)[CH2:15]2)[CH:8]=[C:7]([Cl:6])[CH:12]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67247574HCID 67247574, compound

Product 1

HCID 67246534HCID 67246534, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 10% Sulfuric acid (0.1 ml) and 4-[5-(3,5-dichloro-phenyl)-5-methyl-4,5-dihydro-isoxazol-3-yl]-N-(2,2-dimethyl-[1,3]dioxolane-4-ylmethyl)-2-methylbenzamide (1 g, 1.9 mmol) in methanol (50 ml) was stirred at 70° C. for 4 hours. The solvent was evaporated and the crude mixture was diluted with ethyl acetate (100 ml), washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml×2) and then with water (50 ml). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to give the title compound as a solid (0.7 g). M.p. 98-98° C. LCMS (Method G) 3.65 min, MH+ 491. 1HNMR (CDCl3, 400 MHz): 7.37-7.49 (m, 6H), 6.59 (t, 1H), 4.12 (d, 1H), 3.88 (m, 1H), 3.67 (d, 1H), 3.60 (m, 4H), 2.41 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. additionthe crude mixture was diluted with ethyl acetate (100 ml)
  3. washwashed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml×2)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b6faa01e7d2c49f7b45ab744a2407b1c
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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