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

HRID 729404

반응식

HRID 729404 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 284Formic Acid용매HCID 962Water용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-5bc4535330ff4322868a916993010641
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582627B2

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