Hydrochloric Acid → {[2-Fluoro-4-(4-fluoro-benzyloxy)-phenylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

HRID 1884163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1884163
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[NH2:17].Cl.[C:19]([NH:26][CH2:27][C:28](O)=[O:29])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C1(N=C=NC2CCCCC2)CCCCC1.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:22]([O:21][C:19](=[O:20])[NH:26][CH2:27][C:28](=[O:29])[NH:17][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:7][C:2]=1[F:1])([CH3:25])([CH3:23])[CH3:24]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 221378852-Fluoro-4-(4-fluoro-benzyloxy)-phenylamine

Produkt 1

HCID 69010933{[2-Fluoro-4-(4-fluoro-benzyloxy)-phenylcarbamoyl]-methyl}-carbamic acid tert-butyl esterAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-fluoro-4-(4-fluoro-benzyloxy)-phenylamine (1:1) hydrochloride (272 mg, 1 mmol), Boc-glycine (263 mg, 1.5 mmol), N,N′-dicylcohexylcarbodiimide (206 mg, 1 mmol) and pyridine (127 mg, 1.6 mmol) in ethyl acetate (6 mL) was stirred at room temperature for 3 h. After this time, the reaction mixture wa poured into sodium hydrogen carbonate (saturated), and the mixture extracted with ethyl acetate. The combined organic layers were then washed with brine and dried. Filtration and evaporation afforded the title compound (180 mg, 46%) as a light brown solid after chromatography on silica gel eluting with ethyl acetate: heptane (1:1 to 4:1). MS: m/e=393.1 (M++H).

Aufarbeitung

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe combined organic layers were then washed with brine
  3. customdried
  4. filtrationFiltration and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0cbb6872817948b88f05a0cb3249ad60
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06762320B2

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