Hydrochloric Acid → 3-hydroxy-2-hydroxymethyl-2-[4-(9-hydroxy-2-methyl-9-trifluoromethyl-9H-fluoren-4-yl)-pyrazol-1-yl]-propionic acid

HRID 1799043ノート

反応式

HRID 1799043 の反応式
C([O:5][C:6](=[O:32])[CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[C:25]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([OH:30])([C:26](F)([F:28])[F:27])[C:17]=3[CH:16]=[C:15]([CH3:31])[CH:14]=2)[CH:10]=[N:9]1)(C)(C)C.[CH2:33]=[O:34].[F-:35].C([N+](CCCC)(CCCC)CCCC)CCC.Cl.CN(C)[CH:56]=[O:57]>O1CCCC1.O>[OH:34][CH2:33][C:7]([CH2:56][OH:57])([N:8]1[CH:12]=[C:11]([C:13]2[C:25]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([OH:30])([C:26]([F:27])([F:28])[F:35])[C:17]=3[CH:16]=[C:15]([CH3:31])[CH:14]=2)[CH:10]=[N:9]1)[C:6]([OH:5])=[O:32]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6228DimethylformamideHCID 2724141Tetrabutylammonium FluorideHCID 59492691t-butyl[4-(9-hydroxy-2-methyl-9-trifluoromethyl-9H-fluoren-4-yl)-pyrazol-1-yl]-acetate

生成物 1

HCID 594926873-hydroxy-2-hydroxymethyl-2-[4-(9-hydroxy-2-methyl-9-trifluoromethyl-9H-fluoren-4-yl)-pyrazol-1-yl]-propionic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
95 °C

実験手順

To a solution of an optically active form (17.8 g) of t-butyl[4-(9-hydroxy-2-methyl-9-trifluoromethyl-9H-fluoren-4-yl)-pyrazol-1-yl]-acetate and paraformaldehyde (12.0 g) in dimethylformamide (60 ml) was added at room temperature a 1M solution (120 ml) of tetrabutylammonium fluoride in tetrahydrofuran, and the mixture was stirred at 95° C. for 3 hr. To the reaction mixture were added 1N hydrochloric acid (180 ml) and water (90 ml), and the mixture was extracted with ethyl acetate (180 ml). The separated aqueous layer was extracted twice with ethyl acetate (90 ml). The combined organic layer was successively washed once with 1N hydrochloric acid (90 ml), twice with water (90 ml) and once with saturated brine (90 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (15.5 g).

後処理

  1. extractionthe mixture was extracted with ethyl acetate (180 ml)
  2. extractionThe separated aqueous layer was extracted twice with ethyl acetate (90 ml)
  3. washThe combined organic layer was successively washed once with 1N hydrochloric acid (90 ml), twice with water (90 ml) and once with saturated brine (90 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c7efb0ec634941c5b2d6d809a9cb2ba7
出典データセット
uspto-grants-2013_01
特許番号
US08343994B2

反応ノート

読み込み中…