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

HRID 1990269ノート

反応式

HRID 1990269 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-650dfaef34174345bdd4ac77c1a17a81
出典データセット
uspto-grants-2010_01
特許番号
US07642259B2

反応ノート

読み込み中…