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

HRID 864761

반응식

HRID 864761 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-dfaa7bb79f8d45b0a77927ea4c79e08e
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563163

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