1,2-Dichloroethane → HCID 67284804, Verbindung

HRID 389866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389866
[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

Komponenten

4

Edukt 3

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

Produkt 1

HCID 67284804HCID 67284804, Verbindung

Versuchsvorschrift

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+]

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d052d4c43c524787845d848dd1311694
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383615B2

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