Ammonium Chloride → tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-[(2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl)methyl]-1,4-oxazepane-4-carboxylate

HRID 1022800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022800
C[O-].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([CH:12]2[CH:18]([CH2:19][NH:20][C:21](=[O:33])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([O:31]C)=O)[O:17][CH2:16][CH2:15][N:14]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11].[Cl-].[NH4+]>CO>[Cl:4][C:5]1[CH:6]=[C:7]([CH:12]2[CH:18]([CH2:19][N:20]3[C:29](=[O:31])[C:24]4[C:23](=[CH:28][CH:27]=[CH:26][CH:25]=4)[NH:22][C:21]3=[O:33])[O:17][CH2:16][CH2:15][N:14]([C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])[CH2:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 66976641tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-[({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)methyl]-1,4-oxazepane-4-carboxylate

Produkt 1

HCID 66976879tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-[(2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl)methyl]-1,4-oxazepane-4-carboxylateAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 28% solution (0.2 ml) of sodium methoxide in methanol was added dropwise to a solution of tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-[({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)methyl]-1,4-oxazepane-4-carboxylate (190 mg) in methanol (5 mL), and the mixture was stirred at 80° C. for 1 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (135 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ff36ea3383e141479fe23a0f49b1a89f
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722662B2

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