Water → HCID 86684694、化合物

HRID 77554

反応式

HRID 77554 の反応式
[NH2:1][C:2](=[O:22])[CH2:3][NH:4]/[C:5](/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH2:20][OH:21])=[CH:6]\[C:7]([O:9]CC)=O.C[Si]([N:27]=[C:28]=[S:29])(C)C.O>O1CCCC1>[OH:21][CH2:20][CH2:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:5]1[N:4]([CH2:3][C:2]([NH2:1])=[O:22])[C:28](=[S:29])[NH:27][C:7](=[O:9])[CH:6]=1

参加物

5

反応物 3

HCID 962WaterHCID 75297IsothiocyanatotrimethylsilaneHCID 86684693(Z)-Ethyl 3-((2-amino-2-oxoethyl)amino)-3-(2-(2-hydroxyethoxy)phenyl)acrylate

生成物 1

HCID 86684694HCID 86684694、化合物収率 31.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of (Z)-ethyl 3-((2-amino-2-oxoethyl)amino)-3-(2-(2-hydroxyethoxy)phenyl)acrylate (1.0 g, 3.25 mmol) in tetrahydrofuran (15 mL) was added trimethylsilyl isothiocyanate (1.7 g, 12.9 mmol), and the mixture was stirred at 80° C. for 18 hours. The reaction mixture was cooled to room temperature, poured into a flask containing water and extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried and concentrated under reduced pressure to give a yellow solid, which was purified by flash chromatography (2-5% MeOH:CH2Cl2) to give the title compound (330 mg, 31.7%) as a yellow solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured into a flask
  3. extractionextracted with CH2Cl2 (3×100 mL)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow solid, which
  7. customwas purified by flash chromatography (2-5% MeOH:CH2Cl2)

出典と根拠

ORDレコード
ord-3ae7aaaa46f54d2288c5c846c65e079f
出典データセット
uspto-grants-2014_09
特許番号
US08841314B2

関連ノート

読み込み中…