Ibuprofen, (+-)- → HCID 9861357、化合物

HRID 1872788ノート

反応式

HRID 1872788 の反応式
[OH:1][C:2]([CH:4]([C:6]1[CH:15]=[CH:14][C:9]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:8][CH:7]=1)[CH3:5])=[O:3].[C:16]([O:21][CH2:22]Cl)(=[O:20])[CH2:17][CH2:18][CH3:19].C(N(CC)CC)C.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[C:16]([O:21][CH2:22][O:3][C:2](=[O:1])[CH:4]([CH3:5])[C:6]1[CH:7]=[CH:8][C:9]([CH2:10][CH:11]([CH3:12])[CH3:13])=[CH:14][CH:15]=1)(=[O:20])[CH2:17][CH2:18][CH3:19]

参加物

6

反応物 4

HCID 3672Ibuprofen, (+-)-HCID 8471TriethylamineHCID 2725008Chloromethyl butanoateHCID 21226206Ethyl acetate hexane

生成物 1

HCID 9861357HCID 9861357、化合物収率 58%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a stirred solution of ibuprofen (10.16 g, 49 mmol) and chloromethyl butyrate (6.80 g, 1 eq.) in dry dimethylformamide (20 mL), under nitrogen, was dropwise added triethylamine (8.5 mL, 6 g, 1.2 eq). The mixture was heated at 70° C. for four hours, during which time a large amount of precipitate formed; thin layer chromatography (TLC: ethyl acetate:hexane 1:1) showed that all of the acid had reacted. The precipitate was filtered and washed with ethyl acetate. The filtrate was partitioned between water and ethyl acetate. The aqueous phase was washed with a small amount of ethyl acetate and the combined organic phase was washed with water (3 x), 5% solution of sodium bicarbonate (2 x), and brine (2 x), dried with magnesium sulfate and evaporated to give the crude product as a colorless oil (11.6 g). The crude product was distilled at 170° C./1 mm Hg. The pure product was obtained as a colorless oil (8.7 g, 58% yield).

後処理

  1. customformed
  2. customhad reacted
  3. filtrationThe precipitate was filtered
  4. washwashed with ethyl acetate
  5. customThe filtrate was partitioned between water and ethyl acetate
  6. washThe aqueous phase was washed with a small amount of ethyl acetate
  7. washthe combined organic phase was washed with water (3 x), 5% solution of sodium bicarbonate (2 x), and brine (2 x)
  8. dry with materialdried with magnesium sulfate
  9. customevaporated
  10. customto give the crude product as a colorless oil (11.6 g)
  11. distillationThe crude product was distilled at 170° C./1 mm Hg

出典と根拠

ORDレコード
ord-38bc0cc62ebc4d6cbec2af040eaec92a
出典データセット
uspto-grants-2000_08
特許番号
US06110955

反応ノート

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