Acetonitrile → 2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid

HRID 1796133

反応式

HRID 1796133 の反応式
[CH2:1]=[C:2]([CH2:6][C:7]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:8])[C:3]([OH:5])=[O:4].[CH2:15]([S:19]([OH:21])=[O:20])[CH:16]([CH3:18])[CH3:17].C(#N)C>C1(C)C=CC=CC=1>[CH3:17][CH:16]([CH3:18])[CH2:15][S:19]([CH2:1][CH:2]([CH2:6][C:7]([N:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1)=[O:8])[C:3]([OH:5])=[O:4])(=[O:21])=[O:20]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 12672760Isobutyl-sulphinic acidHCID 220540222-Methylene4-morpholin-4-yl-4-oxo-butyric acid

生成物 1

HCID 115659842-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid収率 28%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

A mixture of 2-Methylene-4-morpholin-4-yl-4-oxo-butyric acid (3.98 g, 20 mmol) and isobutyl-sulphinic acid (2.44 g, 20 mmol) were suspended in anhydrous toluene (80 mL) and anhydrous acetonitrile (20 mL). This mixture was warmed to 85° C. and stirred vigorously for 4.5 h. The reaction mixture was allowed to cool to room temperature and concentrated under vacuum. The residue was purified by flash chromatography using a 90 g silica gel column eluting with 10% methanol/CH2Cl2. Recovered 3.7 g of product as an oil. Triturated residue with isopropanol (5 mL)/ether (100 mL). Product began to precipitate out. Cooled this to 5° C. for 17 hrs(overnight). Product was collected by filtration, washed with ether and dried under vacuum to give 2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid as a white solid (1.8 g).

後処理

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash chromatography
  4. washeluting with 10% methanol/CH2Cl2
  5. customRecovered 3.7 g of product as an oil
  6. customto precipitate out
  7. temperatureCooled this to 5° C. for 17 hrs(overnight)
  8. filtrationProduct was collected by filtration
  9. washwashed with ether
  10. customdried under vacuum

出典と根拠

ORDレコード
ord-01136e723d504499b19315b80684ec11
出典データセット
uspto-grants-2006_04
特許番号
US07030116B2

関連ノート

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