Triethylamine → 3-(4(1-(2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-methanesulfonyloxymethyloxazolidin-2-one

HRID 1582360노트

반응식

HRID 1582360 반응식
[CH3:1][C:2]1([CH3:31])[O:6][C@H:5]([C:7]([N:9]2[CH2:14][CH2:13][C:12]([C:15]3[C:20]([F:21])=[CH:19][C:18]([N:22]4[CH2:26][C@H:25]([CH2:27][OH:28])[O:24][C:23]4=[O:29])=[CH:17][C:16]=3[F:30])=[CH:11][CH2:10]2)=[O:8])[CH2:4][O:3]1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][C:2]1([CH3:31])[O:6][C@H:5]([C:7]([N:9]2[CH2:14][CH2:13][C:12]([C:15]3[C:16]([F:30])=[CH:17][C:18]([N:22]4[CH2:26][C@H:25]([CH2:27][O:28][S:40]([CH3:39])(=[O:42])=[O:41])[O:24][C:23]4=[O:29])=[CH:19][C:20]=3[F:21])=[CH:11][CH2:10]2)=[O:8])[CH2:4][O:3]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 207256433-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one

생성물 1

HCID 207256443-(4(1-(2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-methanesulfonyloxymethyloxazolidin-2-one수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4yl)-3,5-difluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one (2.19 g, 5 mM) was dissolved in dry dichloromethane (40 ml) under nitrogen at 0°, and treated with triethylamine (0.81 g, 8 mM). Methanesulfonyl chloride (0.687 g, 6 mM) was added, and stirring continued for 2 hours, allowing the temperature to rise to ambient. Aqueous sodium bicarbonate (5%, 20 ml) was added, and stirring continued for 10 minutes. The organic phase was separated, dried (magnesium sulfate), filtered, and evaporated to dryness. The resulting gum was triturated with diethyl ether (50 ml) and solid filtered to give the title compound (2.4 g). NMR (DMSO-d6) δ: 1.30 (s, 3H); 1.33 (s, 3H); 2.30 (br, 1H); 2.39 (br, 1H); 3.26 (s, 3H); 3.67 (t overlapping m, 2H); 3.82 (dd, 1H); 4.01-4.31 (complex overlapping m, 5H); 4.45 (dd, 1H); 4.51 (dd, 1H); 4.90 (dd, 1H); 5.03 (m, 1H); 5.87 (s, 1H); 7.35 (d, 2H). MS (ESP): 517 (MH+) for C22H26F2N2O8S

후처리

  1. stirringstirring
  2. waitcontinued for 10 minutes
  3. customThe organic phase was separated
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting gum was triturated with diethyl ether (50 ml) and solid
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-e1f5883a1441425494987bfb9c30a06d
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734200B1

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