Potassium Carbonate → methyl 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoate

HRID 1175986노트

반응식

HRID 1175986 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][C@@H:13]([CH3:16])[CH2:14][OH:15])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N:17]1([C:21]([C:23]2[CH:24]=[C:25]([Cl:30])[C:26](Cl)=[N:27][CH:28]=2)=[O:22])[CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:17]1([C:21]([C:23]2[CH:24]=[C:25]([Cl:30])[C:26]([O:1][C:2]3[CH:3]=[C:4]([CH:9]=[C:10]([O:12][C@@H:13]([CH3:16])[CH2:14][OH:15])[CH:11]=3)[C:5]([O:7][CH3:8])=[O:6])=[N:27][CH:28]=2)=[O:22])[CH2:20][CH2:19][CH2:18]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 536296165-(Azetidin-1-ylcarbonyl)-2,3-dichloropyridineHCID 59127187methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

생성물 1

HCID 53629688methyl 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoate수율 121.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
160 °C

실험 절차

A mixture of methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate (2.35 g, 10.39 mmol), 5-(azetidin-1-ylcarbonyl)-2,3-dichloropyridine (2.41 g, 10.39 mmol) and potassium carbonate (2.87 g, 20.8 mmol) in acetonitrile (20 mL) was stirred in a microwave reactor at 160° C. for 6 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), and the solvent removed in vacuo. The crude oil was chromatographed on silica, eluting with 30-100% ethyl acetate in isohexane, to give the desired compound as a yellow oil (5.3 g).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe crude oil was chromatographed on silica
  7. washeluting with 30-100% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-3881904b11f4478ebe0732310c001653
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842694B2

반응 노트

불러오는 중…