Triphenylphosphine → 3-Acetoxy-5-fluoro-6-methoxy-quinoline-4-carboxylic acid methyl ester

HRID 2273201노트

반응식

HRID 2273201 반응식
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:16])[C:13]=2[F:15])[N:8]=[CH:7][C:6]=1[O:17][C:18](=[O:20])[CH3:19])=[O:4].[C:21]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CO.ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16][CH3:21])[C:13]=2[F:15])[N:8]=[CH:7][C:6]=1[O:17][C:18](=[O:20])[CH3:19])=[O:4]

참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 672473533-Acetoxy-5-fluoro-6-hydroxy-quinoline-4-carboxylic acid methyl ester

생성물 1

HCID 672479353-Acetoxy-5-fluoro-6-methoxy-quinoline-4-carboxylic acid methyl ester수율 65.1%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Methanol (0.52 mL, 12.72 mmol, 3.0 eq) is added at room temperature to a stirred solution of 3-acetoxy-5-fluoro-6-hydroxy-quinoline-4-carboxylic acid methyl ester (1.18 g, 4.24 mmol, 1.0 eq) in tetrahydrofuran (50 mL), followed by triphenylphosphine (2.22 g, 12.72 mmol, 3.0 eq) and diethyl azodicarboxylate (1.48 g, 12.72 mmol, 3.0 eq). After 3 hours stirring at room temperature, solvent is evaporated to give a crude product that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 30:1, v/v) to afford 3-acetoxy-5-fluoro-6-methoxy-quinoline-4-carboxylic acid methyl ester as a yellow oil (0.81 g, 65% yield).

후처리

  1. customsolvent is evaporated
  2. customto give a crude product that
  3. customis purified by column chromatography (silica gel, eluent

출처 및 근거

ORD 기록
ord-4dda1d7c20b045c18c0a58200a3d083d
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120822B2

반응 노트

불러오는 중…