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Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetate → Methyl(2Z)-2-{[(benzyloxy)carbonyl]amino}-3-(6-trifluoromethylpyridin-3-yl)acrylate

HRID 491337
ノート
印刷プレビュー

反応式

HRID 491337 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][CH:4]=1.[CH2:13]([O:20][C:21]([NH:23][CH:24](P(OC)(OC)=O)[C:25]([O:27][CH3:28])=[O:26])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH2:13]([O:20][C:21]([NH:23]/[C:24](=[CH:9]\[C:6]1[CH:7]=[N:8][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=1)/[C:25]([O:27][CH3:28])=[O:26])=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetateHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehyde

生成物 1

HCID 57677192Methyl(2Z)-2-{[(benzyloxy)carbonyl]amino}-3-(6-trifluoromethylpyridin-3-yl)acrylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

6-Trifluormethylpyridine-3-carbaldehyde (4.85 g, 27.70 mmol) and methyl {[(benzyloxy)carbonyl]amino}(dimethoxyphosphoryl)acetate (9.17 g, 27.70 mmol, 1.0 equivalent) are dissolved in THF (70 ml) and cooled to −70° C. At −70° C., N,N,N,N-tetramethylguanidine (6.38 g, 55.39 mmol, 6.95 ml, 2.0 equivalents) is slowly added dropwise and then stirred at −70° C. for 4 h and subsequently at RT for 12 h. The reaction mixture is concentrated and then extracted from water with ethyl acetate (2×100 ml), and the combined organic phases are washed with saturated brine and dried over sodium sulphate. The crude product after concentration in vacuo is chromatographed (silica gel, eluent: toluene then toluene/ethyl acetate 10:1). 6.93 g (66% of theory) of the title compound are obtained.

後処理

  1. concentrationThe reaction mixture is concentrated
  2. extractionextracted from water with ethyl acetate (2×100 ml)
  3. washthe combined organic phases are washed with saturated brine
  4. dry with materialdried over sodium sulphate
  5. concentrationThe crude product after concentration in vacuo
  6. customis chromatographed (silica gel, eluent

出典と根拠

ORDレコード
ord-daff95bd46be48e1864252c0799cf579
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07531507B2

反応ノート

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