(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 66602141, Verbindung

HRID 336906

Reaktionsgleichung

Reaktionsgleichung von HRID 336906
[Si:1]([O:8][CH2:9][CH2:10][S:11]([C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=1[CH:22]1[C:27]([C:28]([NH2:30])=O)=[C:26]([CH3:31])[N:25]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=2)[C:24](=[O:42])[NH:23]1)(=[O:13])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1COCC1.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][S:11]([C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=1[CH:22]1[C:27]([C:28]#[N:30])=[C:26]([CH3:31])[N:25]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:39])([F:40])[F:41])[CH:33]=2)[C:24](=[O:42])[NH:23]1)(=[O:13])=[O:12])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 58133772HCID 58133772, Verbindung

Produkt 1

HCID 66602141HCID 66602141, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The reaction was carried out under argon. (rac)-4-{2-[(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)sulfonyl]-4-cyanophenyl}-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxamide (740 mg, 1.18 mmol) was initially charged in dry THF (30 ml), methoxycarbonylsulfamoyltriethylammonium hydroxide (Burgess reagent; 1.699 g, 7.13 mmol; 6 eq.) was added and the mixture was stirred at RT. After 75 min, HPLC control showed complete conversion. The reaction mixture was then taken up in ethyl acetate (150 ml). The organic phase was washed with saturated sodium chloride solution (3×50 ml), dried over solid sodium sulfate, filtered and concentrated. The residue was subjected to flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1). The title compound was obtained as a colorless solid (550 mg, 77% of theory).

Aufarbeitung

  1. washThe organic phase was washed with saturated sodium chloride solution (3×50 ml)
  2. dry with materialdried over solid sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4e2d787ee2cf446c8b76123e5fd73696
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889700B2

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