Sodium hydride → Benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-4-(2,2,2-trifluoroethyl)-1,4-diazepane-1-carboxylate

HRID 967603

Reaktionsgleichung

Reaktionsgleichung von HRID 967603
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][CH:11]1[CH2:17][N:16]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:15][CH2:14][NH:13][C:12]1=[O:28])=[O:9])([CH3:6])([CH3:5])[CH3:4].ClC(Cl)(Cl)S(O[CH2:35][C:36]([F:39])([F:38])[F:37])(=O)=O.ClC(Cl)(Cl)S([O-])(=O)=O>CN(C)C=O>[C:3]([O:7][C:8]([NH:10][CH:11]1[CH2:17][N:16]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:15][CH2:14][N:13]([CH2:35][C:36]([F:39])([F:38])[F:37])[C:12]1=[O:28])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Komponenten

6

Edukt 4

HCID 24758Sodium hydride2×HCID 900272,2,2-Trifluoroethyl trichloromethanesulphonateHCID 22293222TrichloromethanesulfonateHCID 22293224Benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-1,4-diazepane-1-carboxylate

Produkt 1

HCID 22293256Benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-4-(2,2,2-trifluoroethyl)-1,4-diazepane-1-carboxylateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-35 °C

Versuchsvorschrift

Sodium hydride (60% dispersion in mineral oil; 180 mg, 4.43 mmol) was added to a solution of benzyl 6-[(tert-butoxycarbonyl)amino]-5-oxo-1,4-diazepane-1-carboxylate (1.34 g, 3.69 mmol) in N,N-dimethylformamide (25 mL) at −35° C. After 15 min, 2,2,2-trifluoroethyl trichloromethanesulfonate (0.911 mL, 5.54 mmol) was added and the reaction was stirred at −35° C. After 2 h, an additional amount of sodium hydride (100 mg, 2.5 mmol) and trichloromethanesulfonate (0.500 mL, 3.04 mmol) were added. After 18 h, the reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was washed with water (3×), saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (hexanes→30% ethyl acetate/hexanes) gave the title compound (690 mg). MS 446 (M+1).

Aufarbeitung

  1. waitAfter 2 h
  2. waitAfter 18 h
  3. customthe reaction was quenched with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water (3×), saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (hexanes→30% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2df536e858184391a6e80f2416eaf869
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953790B2

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