Sodium Bicarbonate → HCID 67313552、化合物

HRID 1010881ノート

反応式

HRID 1010881 の反応式
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH2:23]([O:30][C:31](=[O:41])[N:32]([CH2:34][C:35](N(OC)C)=[O:36])[CH3:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:23]([O:30][C:31](=[O:41])[N:32]([CH2:34][C:35]([C:13]1[CH:14]=[CH:15][C:10]([C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])[CH3:9])=[CH:11][CH:12]=1)=[O:36])[CH3:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 56973617(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamateHCID 86625210HCID 86625210、化合物HCID 178418339Butyllithium

生成物 1

HCID 67313552HCID 67313552、化合物収率 12.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

200 mg of the compound [1-1] was dissolved in 4 mL of tetrahydrofuran, and the mixture was cooled to −78° C. and then 626 μL of n-butyllithium (2.66 M hexane solution) was added thereto. After a 1 hour stirring at the same temperature, 0.6 mL of tetrahydrofuran solution containing 177 mg of the compound [2-1] was added thereto, and the mixture was further stirred for 2 hours. To the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=6/4), to obtain 36.2 mg of benzyl[2-(4-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}phenyl)-2-oxoethyl]methylcarbamate [2-2] (hereinafter, referred to as the compound [2-2]) as a colorless oily product.

後処理

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe resulting organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=6/4)

出典と根拠

ORDレコード
ord-c07d319c480f47ae942c2aa3366d6b13
出典データセット
uspto-grants-2011_07
特許番号
US07977336B2

反応ノート

読み込み中…