Diethyl Ether → HCID 178459293、化合物

HRID 892126ノート

反応式

HRID 892126 の反応式
[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:14][C:15]=3[N:16]([CH2:21]C(OC)=O)[C:17]2=[O:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][Mg]Br.[Cl-:34].[NH4+].C([O:38][CH2:39][CH3:40])C>O1CCCC1>[ClH:34].[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:14][C:15]=3[N:16]([CH2:21][C:39]([OH:38])([CH3:40])[CH3:31])[C:17]2=[O:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573、化合物HCID 178501545HCID 178501545、化合物

生成物 1

HCID 178459293HCID 178459293、化合物収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Compound 77c (670 mg, 1.65 mmol) obtained in Example 77 was dissolved in tetrahydrofuran (7 mL), to the solution was added methyl magnesium bromide (2.75 mL, a 3.0 mol/L solution in diethyl ether, 5.0 equivalents) under ice cooling, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture was added saturated aqueous ammonium chloride, and the mixture was warmed to room temperature and stirred for 10 minutes. The reaction mixture was extracted with chloroform, and the resulting organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform:methanol=99:1). The product was converted into hydrochloride with a 4 mol/L solution of hydrogen chloride in dioxane, and then, after the solvent was evaporated, the product was recrystallized from ethyl acetate to obtain the title compound (460 mg, 68%).

後処理

  1. extractionThe reaction mixture was extracted with chloroform
  2. washthe resulting organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=99:1)
  6. customafter the solvent was evaporated
  7. customthe product was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-ca98771b1f4c4510809b0c7bfd7b4c39
出典データセット
uspto-grants-2006_02
特許番号
US07005430B2

反応ノート

読み込み中…