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

HRID 729404

反応式

HRID 729404 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 962Water溶媒

実験手順

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 afford a 5.4 g of the title compound as a clear oil. MS CI: m/z 228 (MH+).

後処理

  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

出典と根拠

ORDレコード
ord-5bc4535330ff4322868a916993010641
出典データセット
uspto-grants-2009_09
特許番号
US07582627B2

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