3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde → 5-[2-Benzyloxy-4-(hydroxypyridin-2-yl-methyl)-phenyl]1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 660809ノート

反応式

HRID 660809 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N:17]1[CH2:21][C:20](=[O:22])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[S:18]1(=[O:30])=[O:29])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[Mg]Br>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]([OH:13])[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=2)[CH:14]=[CH:15][C:16]=1[N:17]1[S:18](=[O:29])(=[O:30])[N:19]([CH2:23][CH2:24][Si:25]([CH3:26])([CH3:27])[CH3:28])[C:20](=[O:22])[CH2:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 866250473-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehydeHCID 178419629HCID 178419629、化合物

生成物 1

HCID 688429995-[2-Benzyloxy-4-(hydroxypyridin-2-yl-methyl)-phenyl]1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde (Example 81, step B) (75 mg, 0.17 mmol) in anhydrous THF (4 mL) at −78° C. is added dropwise 2-pyridyl magnesium bromide (0.25M in THF, 1.36 mL, 0.34 mmol). The reaction is stirred at −78° C. for 1 h, then is quenched with saturated NH4Cl. The mixture is extracted with EtOAc and the organic phase is dried over MgSO4. The solvent is removed under reduced pressure and the crude material is purified by column chromatography using a gradient of 0-50% EtOAc/hexane to afford the title compound as a colorless oil: (M−H)−=526.

後処理

  1. customis quenched with saturated NH4Cl
  2. extractionThe mixture is extracted with EtOAc
  3. dry with materialthe organic phase is dried over MgSO4
  4. customThe solvent is removed under reduced pressure
  5. customthe crude material is purified by column chromatography

出典と根拠

ORDレコード
ord-fb8065d7244c48db97c9eeffd2667551
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

反応ノート

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