Pyridine → 2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide

HRID 1836463

반응식

HRID 1836463 반응식
[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8](Cl)=[O:9])[C:4](=[O:11])[O:3]1.[F:13][C:14]1[CH:23]=[CH:22][C:17]([CH2:18][NH:19][O:20][CH3:21])=[CH:16][CH:15]=1.N1C=CC=CC=1>ClCCl>[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([N:19]([CH2:18][C:17]2[CH:22]=[CH:23][C:14]([F:13])=[CH:15][CH:16]=2)[O:20][CH3:21])=[O:9])[C:4](=[O:11])[O:3]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 12147060Benzenemethanamine, 4-fluoro-N-methoxy-HCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

생성물 1

HCID 730332332-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide수율 93.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
22 °C

실험 절차

A solution of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride (2.45 g, 12.9 mmol) in dichloromethane (15 ml) was added dropwise over 10 minutes to a cold (0-5° C.) mixture of N-4-fluorobenzyl-O-methyl-hydroxylamine (2.0 g, 12.9 mmol) and pyridine (2.1 ml, 25.7 mmol) in dichloromethane (50 ml). The cooling bath was then removed and the solution was stirred at 22° C. for 30 minutes. The reaction mixture was then quenched by the addition of water and ethyl acetate. The organic phase was washed successively with 0.1 N hydrochloric acid, saturated sodium bicarbonate, brine and dried (magnesium sulfate). Evaporation of the solvent and chromatography of the residue on silica gel (toluene-ethyl acetate, 8:2) gave 3.72 g (93% yield) of the title amide as white crystals after recrystallization from ethyl acetate/hexanes. Differential scanning calorimetry shows a sharp endotherm at 107° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.75 (6H, s), 3.68 (3H, s), 4.79 (2H, s), 6.38 (1H, s), 7.0 (2H, m), 7.34 (2H, m). 13CNMR 100 MHz (CDCl3) δ (ppm): 26.81, 48.43, 63.03, 94.48, 114.22, 115.31, 115.56, 130.47, 132.03, 146.95, 161.21, 162.46, 163.65, 164.43. 19FNMR 377 MHz(CDCl3) δ (ppm): 114.97. Anal. calcd for C15H16FNO5: C, 58.25; H, 5.21; N, 4.52; Found: C, 58.33; H, 5.38; N, 4.51.

후처리

  1. customThe cooling bath was then removed
  2. customThe reaction mixture was then quenched by the addition of water and ethyl acetate
  3. washThe organic phase was washed successively with 0.1 N hydrochloric acid, saturated sodium bicarbonate, brine
  4. dry with materialdried (magnesium sulfate)
  5. customEvaporation of the solvent and chromatography of the residue on silica gel (toluene-ethyl acetate, 8:2)

출처 및 근거

ORD 기록
ord-24d39672dd2b413c828b24c1270d7ec4
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777440B2

연결된 노트

불러오는 중…