Sulfuric Acid → rac-ethyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate

HRID 604809ノート

反応式

HRID 604809 の反応式
[CH2:1]([O:3][C:4]([C@@:6]1([NH:11]C(OC(C)(C)C)=O)[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].S(=O)(=O)(O)O>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C@@:6]1([NH2:11])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 10658673Ethyl (1R,2S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenylcyclopropanecarboxylate

生成物 1

HCID 10820795rac-ethyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
8 °C

実験手順

A suspension of 5.11 g (20.0 mmol) of (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid ethyl ester (commercially available from Synthetech Oregon, USA) in 1.94 mL of ethyl acetate was cooled to 8° C. using an ice bath. Then a solution of 2.17 g (21.0 mmol) of sulfuric acid in 4.0 mL of ethyl acetate was added in 5 min. The ice bath was removed and the reaction mixture was stirred for 30 min at room temperature and 1 h at 50° C. The reaction mixture was then cooled to room temperature and used in the next step without further purification.

後処理

  1. customThe ice bath was removed
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customused in the next step without further purification

出典と根拠

ORDレコード
ord-5b44c30be31f4a6fb2d233d6ed607855
出典データセット
uspto-grants-2011_03
特許番号
US07910728B2

反応ノート

読み込み中…