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Sodium Bicarbonate → HCID 178462434、化合物

HRID 1937162
ノート
印刷プレビュー

反応式

HRID 1937162 の反応式
[O:1]=[CH:2]/[CH:3]=[CH:4]/[CH:5]=[CH:6]/[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[C@:23]([OH:38])([C@H:30]([S:32][CH:33]([CH2:36]O)[CH2:34][OH:35])[CH3:31])[CH2:24][N:25]1[CH:29]=[N:28][CH:27]=[N:26]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[C:11]([C:10]1[CH:13]=[CH:14][C:7](/[CH:6]=[CH:5]/[CH:4]=[CH:3]/[C@H:2]2[O:35][CH2:34][C@H:33]([S:32][C@H:30]([CH3:31])[C@:23]([C:17]3[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=3[F:15])([OH:38])[CH2:24][N:25]3[CH:29]=[N:28][CH:27]=[N:26]3)[CH2:36][O:1]2)=[CH:8][CH:9]=1)#[N:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 10594623(2R,3R)-2-(2,4-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]-thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanolHCID 106550534-[(1E,3E)-5-Oxo-1,3-pentadienyl]benzonitrile

生成物 1

HCID 178462434HCID 178462434、化合物収率 81.3%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

実験手順

A mixture of 240 mg (1.31 mmol) of 4-[(1E,3E)-5-oxo-1,3-pentadienyl]benzonitrile [prepared as described in Step 1(i) above], 392 mg (1.09 mmol) of (2R,3 R)-2-(2,4-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol [prepared as described in Japanese Patent Application (Kokai) Hei 8-333350)], 249 mg (1.31 mmol) of p-toluenesulfonic acid monohydrate, 16 ml of dichloromethane and 3.9 a of molecular sieves 4A was stirred at ambient temperature over night. Aqueous sodium hydrogen carbonate was then added to the reaction mixture and insoluble material was removed by filtration. The resulting filtrate was extracted with ethyl acetate and the organic layer was dried and then concentrated. The resulting residue was purified by chromatography on silica Gel (15 g) column using a 1:1 mixture of ethyl acetate and hexane as the eluant to give 465 mg (yield 81%) of the title compound as a solid. This solid was recrystallized from a mixture of ethyl acetate and hexane to afford crystals.

後処理

  1. customprepared
  2. customwas removed by filtration
  3. extractionThe resulting filtrate was extracted with ethyl acetate
  4. customthe organic layer was dried
  5. concentrationconcentrated
  6. customThe resulting residue was purified by chromatography on silica Gel (15 g) column
  7. additiona 1:1 mixture of ethyl acetate and hexane as the eluant

出典と根拠

ORDレコード
ord-814ea813070b4c65a2eb21996f0efb31
出典データセット
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06392082B1

反応ノート

読み込み中…

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