Ethyl oxoacetate → Ethyl 2-((4-chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl)amino)acetate

HRID 588871ノート

反応式

HRID 588871 の反応式
[Cl:1][C:2]1[C:8]([C:9]2([CH3:12])[CH2:11][CH2:10]2)=[CH:7][C:5]([NH2:6])=[C:4]([O:13][CH3:14])[CH:3]=1.[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH:16]=O.C([BH3-])#N.[Na+]>CO.CC(O)=O>[Cl:1][C:2]1[C:8]([C:9]2([CH3:12])[CH2:10][CH2:11]2)=[CH:7][C:5]([NH:6][CH2:16][C:15]([O:19][CH2:20][CH3:21])=[O:18])=[C:4]([O:13][CH3:14])[CH:3]=1

参加物

6

反応物 3

HCID 70211Ethyl oxoacetateHCID 5003444Sodium cyanoborohydrideHCID 904558234-Chloro-2-methoxy-5-(1-methylcyclopropyl)aniline

生成物 1

HCID 90456166Ethyl 2-((4-chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl)amino)acetate収率 100.3%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 887Methanol溶媒

実験手順

To a solution of 4-chloro-2-methoxy-5-(1-methylcyclopropyl)aniline (450 mg, 2.13 mmol) in MeOH (20 mL) at RT, AcOH (3 drops) and ethyl glyoxalate (326 mg, 3.19 mmol, 50% in toluene) were added. The mixture was stirred at RT for 2 h and then sodium cyanoborohydride (403 mg, 6.39 mmol) was added to the mixture. The resulting mixture was stirred at 50° C. for 16 h. The mixture was allowed to cool to RT, and partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford the crude product (636 mg). ESI-MS m/z: 298.2[M+H]+.

後処理

  1. stirringThe resulting mixture was stirred at 50° C. for 16 h
  2. temperatureto cool to RT
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f234432b94514c0daab7cd99b2ab5ce2
出典データセット
uspto-grants-2016_01
特許番号
US09227978B2

反応ノート

読み込み中…