Methanol → 2-Cyclopropylamino-4,5-difluorobenzoic acid methyl ester

HRID 10319

Reaktionsgleichung

Reaktionsgleichung von HRID 10319
[CH:1]1([NH:4][C:5]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:6]=2[C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.Cl[CH2:17]Cl.CO.C[Si](C=[N+]=[N-])(C)C>O.C(O)=O>[CH3:17][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:11]([F:15])[C:12]([F:14])=[CH:13][C:5]=1[NH:4][CH:1]1[CH2:2][CH2:3]1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 6344DichloromethaneHCID 167693TrimethylsilyldiazomethaneHCID 149974732-Cyclopropylamino-4,5-difluorobenzoic acid

Produkt 1

HCID 210411932-Cyclopropylamino-4,5-difluorobenzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-cyclopropylamino-4,5-difluorobenzoic acid (Example 5a) (6.0 g, 28.1 mmol), dichloromethane (100 mL), and methanol (20 mL) is added (trimethylsilyl)diazomethane (2.9 M solution in hexane) dropwise until the evolution of gas stops. The solution is stirred at room temperature for 0.5 hour and 88% formic acid is added dropwise until the evolution of gas again stops. Water is added, and the solution is extracted with dichloromethane, dried over MgSO4, filtered, and the solvent removed under reduced pressure. The residue is purified by silica gel column chromatography using hexane/EtOAc (9:1) as the eluent to afford a 5.4 g of the title compound as a clear oil. MS CI: m/z 228 (MH+).

Aufarbeitung

  1. extractionthe solution is extracted with dichloromethane
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-af712a0070fe42688003d15eb8dd1bab
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094780B1

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