Water → 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[(3S)-tetrahydrofuran-3-yloxy]benzoic acid

HRID 1990007ノート

反応式

HRID 1990007 の反応式
[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:30])[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([O:24][C@H:25]4[CH2:29][CH2:28][O:27][CH2:26]4)[CH:23]=3)[C:17]([O:19]C)=[O:18])=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].O>C1COCC1.CO>[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([Cl:30])[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([O:24][C@H:25]4[CH2:29][CH2:28][O:27][CH2:26]4)[CH:23]=3)[C:17]([OH:19])=[O:18])=[N:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 53629676Methyl 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate

生成物 1

HCID 536296753-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[(3S)-tetrahydrofuran-3-yloxy]benzoic acid収率 97.1%

試薬・触媒・溶媒 2

HCID 887Methanol触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate (3.75 g, 8.68 mmol) was dissolved in THF (40 mL), 1N sodium hydroxide (8.68 mL, 8.68 mmol) was added followed by water (40 mL) and methanol (1 drop) and the resultant solution stirred at RT for 3 hours. The organics were removed in vacuo, the aqueous solution filtered and extracted with ethyl acetate (30 mL). The aqueous layer was acidified with 2N hydrochloric acid, extracted with ethyl acetate (3×50 mL), and the organic extracts washed with water (10 mL), brine (10 mL) then evaporated to dryness to give the desired material as a white foam (3.53 g).

後処理

  1. customThe organics were removed in vacuo
  2. filtrationthe aqueous solution filtered
  3. extractionextracted with ethyl acetate (30 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washthe organic extracts washed with water (10 mL), brine (10 mL)
  6. customthen evaporated to dryness

出典と根拠

ORDレコード
ord-5292d50f4ed04f2196018e786bf0b3cd
出典データセット
uspto-grants-2010_01
特許番号
US07642263B2

反応ノート

読み込み中…