1,2-Dichloroethane → HCID 67284804、化合物

HRID 389866ノート

反応式

HRID 389866 の反応式
[O:1]=[C:2]1[NH:5][C@H:4]([C:6]([OH:8])=[O:7])[CH2:3]1.ClCCCl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:5]2[C:2](=[O:1])[CH2:3][C@H:4]2[C:6]([OH:8])=[O:7])=[CH:16][CH:15]=1

参加物

4

反応物 3

HCID 111,2-DichloroethaneHCID 742994-Chlorophenylboronic acidHCID 13469007(2S)-4-Oxoazetidine-2-carboxylic acid

生成物 1

HCID 67284804HCID 67284804、化合物

実験手順

To a stirred suspension of (S)-4-oxo-azetidine-2-carboxylic acid (1.0 g; 8.689 mmol) in 1,2-dichloroethane (35 mL) 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) (3.1 mL; 20.854 mmol) is added at room temperature. After 10 min di-μ-hydroxy-bis[N,N,N′,N′-tetramethylenediamine)-copper (II) chloride (Cu-TMEDA) (1.614 g; 3.476 mmol) is added to the clear solution. The mixture is stirred for 10 min and 4-chlorophenylboronic acid (1.495 g; 9.558 mmol) is added. After 20 hours, solvent is evaporated in vacuo, the concentrate taken up in saturated sodium bicarbonate solution (150 mL) and the aqueous layer is washed with ethyl acetate (3×100 mL). The aqueous layer is treated with 1N hydrochloric acid to pH 2 and extracted with ethyl acetate (3×100 mL). Combined organic extracts washed with brine (2×50 mL), dried over anhydrous sodium sulfate and solvent removed in vacuo to give the title compound as an off-white solid, m/z 226 [M+H+]

後処理

  1. additionis added at room temperature
  2. waitAfter 20 hours
  3. customsolvent is evaporated in vacuo
  4. washthe aqueous layer is washed with ethyl acetate (3×100 mL)
  5. additionThe aqueous layer is treated with 1N hydrochloric acid to pH 2
  6. extractionextracted with ethyl acetate (3×100 mL)
  7. washCombined organic extracts washed with brine (2×50 mL)
  8. dry with materialdried over anhydrous sodium sulfate and solvent
  9. customremoved in vacuo

出典と根拠

ORDレコード
ord-d052d4c43c524787845d848dd1311694
出典データセット
uspto-grants-2013_02
特許番号
US08383615B2

反応ノート

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