Ethyl chloroformate → 4-Fluoro-2-{2-fluoro-4-[(3-oxopiperazin-1-yl)carbonyl]phenoxy}-5-ethylphenyl ethyl carbonate

HRID 389983ノート

反応式

HRID 389983 の反応式
[CH2:1]([C:3]1[C:25]([F:26])=[CH:24][C:6]([O:7][C:8]2[CH:22]=[CH:21][C:11]([C:12]([N:14]3[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]3)=[O:13])=[CH:10][C:9]=2[F:23])=[C:5]([O:27][CH3:28])[CH:4]=1)[CH3:2].[OH-:29].[K+].[CH2:31]([O:33]C(Cl)=O)[CH3:32]>C(#N)C>[C:28](=[O:29])([O:33][CH2:31][CH3:32])[O:27][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[C:25]([F:26])=[CH:24][C:6]=1[O:7][C:8]1[CH:22]=[CH:21][C:11]([C:12]([N:14]2[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]2)=[O:13])=[CH:10][C:9]=1[F:23]

参加物

5

反応物 3

HCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 671162484-[4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]piperazin-2-one

生成物 1

HCID 513565044-Fluoro-2-{2-fluoro-4-[(3-oxopiperazin-1-yl)carbonyl]phenoxy}-5-ethylphenyl ethyl carbonate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 4-[4-(4-ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzoyl]piperazin-2-one (20 mg, 0.053 mmol; which may be prepared as described in D3) in acetonitrile (550 μL) was added KOH (3 mg, 0.053 mmol) followed by ethylchlorocarbonate (6 μL, 0.058 mmol). After 1 hour at room temperature, the mixture was quenched with water. The aqueous layer was extracted twice with ethyl acetate. The organic phase was dried over sodium sulphate, filtered and concentrated under vacuum. The residue was purified by preparative thin layer chromatography on silica gel, using dichloromethane/methanol (95:5) as eluent. The title product was obtained as a white solid (11 mg, 46%).

後処理

  1. customthe mixture was quenched with water
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by preparative thin layer chromatography on silica gel

出典と根拠

ORDレコード
ord-4e9787902e424e06ab405efcccdf09a7
出典データセット
uspto-grants-2013_02
特許番号
US08383621B2

反応ノート

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