Dimethyl Sulfoxide → 3-[(S)-(4-chlorophenyl)(3-oxoazetidin-1-yl)methyl]benzonitrile

HRID 603007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 603007
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([N:27]2[CH2:30][CH:29]([OH:31])[CH2:28]2)[C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])=[CH:14][CH:13]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([N:27]2[CH2:28][C:29](=[O:31])[CH2:30]2)[C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])=[CH:14][CH:13]=1

Komponenten

8

Edukt 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 576121723-[(S)-(4-chlorophenyl)(3-hydroxyazetidin-1-yl)methyl]benzonitrile

Produkt 1

HCID 670554063-[(S)-(4-chlorophenyl)(3-oxoazetidin-1-yl)methyl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of 21.1 mL (0.24 mol) of oxalyl chloride in 500 mL CH2Cl2, a solution of 34.2 mL (0.48 mol) of DMSO in 50 mL CH2Cl2 was added slowly at −78° C. After the reaction mixture was stirred for 30 min., a solution of 36.02 g (0.12 mol) of 3-[(S)-(4-chlorophenyl)(3-hydroxyazetidin-1-yl)methyl]benzonitrile in 50 mL of CH2Cl2 was added and stirred for another 45 min. Then 82.8 mL (0.60 mol) of triethylamine was added and the mixture was stirred for 30 min. at −78° C. The mixture was warmed to rt and stirring continued for 30 min. Then the mixture was poured into 1000 mL of ether and 200 mL of aq NaHCO3. The water layer was extracted with two 200 mL portions of ether. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography with hexanes/ethyl acetate to afford the title compound as a white solid; 1H-NMR(CDCl3) δ 4.03-4.07(m, 4H), 4.65(s, 1H), 7.33-7.43 (m, 4H), 7.45 (t, 1H, J=7.8 Hz), 7.56 (d, 1H, J=7.5 Hz), 7.72 (d, 1H, J=7.5 Hz), 7.81 (s, 1H); Mass Spectrum: m/e=297, (M+1, 35Cl), 299 (M+1, 37Cl).

Aufarbeitung

  1. stirringstirred for another 45 min
  2. stirringthe mixture was stirred for 30 min. at −78° C
  3. stirringstirring
  4. waitcontinued for 30 min
  5. extractionThe water layer was extracted with two 200 mL portions of ether
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography with hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2e9e3e8d3226423cb6348ddc4fb9b2a4
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906652B2

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