Triethylamine → HCID 68686408, Verbindung

HRID 2216660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2216660
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].CCN(CC)CC.[CH:15]1([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=2)[CH2:17][CH2:16]1>O1CCOCC1.O>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][S:26]([C:23]1[CH:22]=[CH:21][C:20]([O:19][CH2:18][CH:15]2[CH2:16][CH2:17]2)=[CH:25][CH:24]=1)(=[O:28])=[O:27]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 113686084-(cyclopropylmethoxy)benzenesulfonyl Chloride

Produkt 1

HCID 68686408HCID 68686408, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of 7.125 g (56.75 mmol) of glycine methylester hydrochloride in 60 ml of dioxane and 24 ml of H2O, 15 ml (107.8 mmol) of Et3N and then a solution of 10 g (40.53 mmol) of 4-cyclopropylmethoxy-benzenesulfonyl chloride in 10 ml of dioxane are added dropwise at 0–5° C. After stirring for 3 h at r.t., the reaction is quenched with ice water and the mixture is extracted with AcOEt. The combined extracts are washed with H2O, brine, dried over MgSO4 and concentrated under reduced pressure to give the title compound as a colorless solid; 1H-NMR (400 MHz, CDCl3): 0.3–0.40 (m, 2H), 0.65–0.72 (m, 2H), 1.20–1.35(m, 1H), 3.65 (m, 3H), 3.77 (d, 2H, J=5.04 Hz), 3.86 (d, 2H, J=7.08 Hz), 4.98 (brs, 1H), 6.96 (d, 2H, J=8.52 Hz), 7.77 (d, 2H, J=8.52 Hz).

Aufarbeitung

  1. customthe reaction is quenched with ice water
  2. extractionthe mixture is extracted with AcOEt
  3. washThe combined extracts are washed with H2O, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-55ec39c802234ab78efdc56becf0e773
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112611B2

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