Ethyl Acetate → N-{(2R)-2-hydroxy-3-[(1-methyl-2,2-dioxo-2,3-dihydro-1H-2,1-benzisothiazol-5-yl)amino]propyl}acetamide

HRID 840195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 840195
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-])=O)=[CH:10][C:5]=2[CH2:4][S:3]1(=[O:15])=[O:14].CCOC(C)=O.[O:22]1[CH2:24][C@@H:23]1[CH2:25][NH:26][C:27](=[O:29])[CH3:28].FC(F)(F)S([O-])(=O)=O.[Mg+2].FC(F)(F)S([O-])(=O)=O>[Pd].CC#N>[OH:22][C@H:23]([CH2:24][NH:11][C:9]1[CH:8]=[CH:7][C:6]2[N:2]([CH3:1])[S:3](=[O:15])(=[O:14])[CH2:4][C:5]=2[CH:10]=1)[CH2:25][NH:26][C:27](=[O:29])[CH3:28]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 2734125Magnesium trifluoromethanesulfonateHCID 11051615Acetamide, N-[(2S)-oxiranylmethyl]-HCID 155387111-Methyl-5-nitro-1,3-dihydrobenzo[c]isothiazole 2,2-dioxide

Produkt 1

HCID 15538712N-{(2R)-2-hydroxy-3-[(1-methyl-2,2-dioxo-2,3-dihydro-1H-2,1-benzisothiazol-5-yl)amino]propyl}acetamideAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 23938PalladiumLösungsmittel

Versuchsvorschrift

The product of Step 1 (0.20 g, 0.88 mmol) is dissolved into EtOAc (30 mL) in a Parr bottle and 10% Pd/C (100 mg) added under nitrogen. The mixture is hydrogenated on a Parr apparatus for 2 hrs at 30 psi. Filtration and evaporation of solvent gave a white solid. This material is added to a mixture of N-[(2S)oxiranylmethyl] acetamide (0.81 g, 7.0 mmol) and magnesium trifluoromethanesulfonate (0.42 g, 1.3 mmol) in dry CH3CN (10 mL) at room temperature. After 20 hrs solvent is evaporated and the residue purified by chromatography (4%MeOH/CH2Cl2) to give a foamy solid (0.23 g, 79%). HRMS (FAB) calcd for C13H19N3O4S +H1 314.1174, found 314.1174.

Aufarbeitung

  1. additionadded under nitrogen
  2. filtrationFiltration and evaporation of solvent
  3. customgave a white solid
  4. customAfter 20 hrs solvent is evaporated
  5. customthe residue purified by chromatography (4%MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-cb73701bb7524c129e9fef26afd4297e
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06365612B2

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