3-(Chloromethyl)-3-methyloxetane → HCID 178490659, 화합물

HRID 78510

반응식

HRID 78510 반응식
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Cl[CH2:29][C:30]1([CH3:34])[CH2:33][O:32][CH2:31]1>CN(C)C=O.O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:29][C:30]2([CH3:34])[CH2:33][O:32][CH2:31]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 3

HCID 791123-(Chloromethyl)-3-methyloxetaneHCID 23665647Potassium tert-butoxideHCID 87094486n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

생성물 1

HCID 178490659HCID 178490659, 화합물

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 8857Ethyl Acetate용매HCID 21974620tetrahydrofuran N,N-dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of Example 244A (0.75 g, 2.31 mmol) in N,N-dimethylformamide/tetrahydrofuran (1:4, 20 mL) were added potassium tert-butoxide (0.39 g, 3.46 mmol), tetrabutylammonium iodide (0.09 mg, 0.23 mmol) and commercially available 3-(chloromethyl)-3-methyloxetane (TCI, 0.28 g, 2.31 mmol). The reaction mixture was stirred at 80° C. for 16 hours, cooled, diluted with ethyl acetate (20 mL) and quenched with saturated aqueous NaHCO3 (20 mL). The aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with water (1×25 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.24 (s, 3H), 1.33 (s, 9H), 3.77 (s, 3H), 4.19 (d, J=6.1 Hz, 2H), 4.38 (s, 2H), 4.69 (d, J=6.1 Hz, 2H), 7.10 (d, J=9.2 Hz, 1H), 7.29 (s, 1H), 7.44 (dd, J=9.0, 2.9 Hz, 1H), 7.58 (d, J=2.7 Hz, 1H); MS (ESI+) m/z 409 (M+H)+; Anal. Calculated for C20H25ClN2O3S: C, 58.74; H, 6.16; N, 6.85. Found: C, 58.92; H, 6.04; N, 6.84.

후처리

  1. temperaturecooled
  2. customquenched with saturated aqueous NaHCO3 (20 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  4. washThe combined organic layers were washed with water (1×25 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-7dbcfb7fde2e4fee82ed5a7daacd9dff
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841334B2

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