Triethylamine → Tert-butyl {[3-morpholin-4-yl-1-(propylsulfonyl)azetidin-3-yl]methyl}carbamate

HRID 2100317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2100317
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].[N:8]1([C:14]2([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:17][NH:16][CH2:15]2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C(N(CC)CC)C.CN(C)CCN>ClCCl>[N:8]1([C:14]2([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:17][N:16]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[CH2:15]2)[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 662791-Propanesulfonyl chlorideHCID 57798317HCID 57798317, Verbindung

Produkt 1

HCID 57798321Tert-butyl {[3-morpholin-4-yl-1-(propylsulfonyl)azetidin-3-yl]methyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Propane-1-sulfonyl chloride (0.44 ml, 3.9 mmol) was added to tert-butyl [(3-morpholin-4-ylazetidin-3-yl)methyl]carbamate (0.71 g, 2.6 mmol) and triethylamine (0.91 g, 6.5 mmol) in dichloromethane (9 ml) at 0° C. The reaction was then stirred at room temperature for 30 mins before quenching with N,N-dimethylethylenediamine (0.5 eq). The resulting mixture was partitioned between dichloromethane and water. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated to dryness to give crude tert-butyl {[3-morpholin-4-yl-1-(propylsulfonyl)azetidin-3-yl]methyl}carbamate which was used without further purification m/z (M++H) 378.

Aufarbeitung

  1. customThe resulting mixture was partitioned between dichloromethane and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-02569a0775b7493788368ae632421285
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572792B2

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