Acetonitrile → 4-Isopropyl-6-methoxy-2-saccharinylmethyl 3,5-dimethylisoxazole-4-carboxylate

HRID 864761

Reaction equation

HRID 864761 reaction equation
C(#N)C.C(N(CC)C(C)C)(C)C.[CH3:13][C:14]1[C:18]([C:19]([OH:21])=[O:20])=[C:17]([CH3:22])[O:16][N:15]=1.Cl[CH2:24][N:25]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][C:31]([O:40][CH3:41])=[CH:32][C:33]=2[CH:37]([CH3:39])[CH3:38])[S:26]1(=[O:28])=[O:27]>C(OCC)(=O)C>[CH3:13][C:14]1[C:18]([C:19]([O:21][CH2:24][N:25]2[C:35](=[O:36])[C:34]3[C:29](=[CH:30][C:31]([O:40][CH3:41])=[CH:32][C:33]=3[CH:37]([CH3:39])[CH3:38])[S:26]2(=[O:27])=[O:28])=[O:20])=[C:17]([CH3:22])[O:16][N:15]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 756363,5-Dimethylisoxazole-4-carboxylic acidHCID 81531DiisopropylethylamineHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 152255274-Isopropyl-6-methoxy-2-saccharinylmethyl 3,5-dimethylisoxazole-4-carboxylateYield 10%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetonitrile (3 ml), followed by N,N-diisopropylethylamine (0.26 ml, 1.5 mmol) were added to 3,5-dimethylisoxazole-4-carboxylic acid (0.21 g, 1.5 mmol). The mixture was stirred for 5 minutes, then 2-chloromethyl-4-isopropyl-6-methoxysaccharin (0.30 g, 1 mmol) was added. The reaction mixture was stirred at room temperature for 18 hours, diluted with ethyl acetate (75 ml) and washed with saturated NaHCO3. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative layer chromatography eluting with CH2Cl2 (100%) to afford 0.041 g (10%) of 4-isopropyl-6-methoxy-2-saccharinylmethyl 3,5-dimethylisoxazole-4-carboxylate as a white solid, m.p. 136.8°-139.1° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. washwashed with saturated NaHCO3
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative layer chromatography
  7. washeluting with CH2Cl2 (100%)

Sources & evidence

ORD record
ord-dfaa7bb79f8d45b0a77927ea4c79e08e
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Linked notes

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