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N,N-Dimethylaniline → (2e)-3-{2,6-Difluoro-4-[(isopropoxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate

HRID 1179482
ノート
印刷プレビュー

反応式

HRID 1179482 の反応式
C1(C)C=CC(S([NH:10][N:11]=[CH:12][C:13](Cl)=[O:14])(=O)=O)=CC=1.[F:17][C:18]1[CH:19]=[C:20]([NH:29][C:30](=[O:35])[O:31][CH:32]([CH3:34])[CH3:33])[CH:21]=[C:22]([F:28])[C:23]=1/[CH:24]=[CH:25]/[CH2:26][OH:27].CN(C)C1C=CC=CC=1.C(N(CC)CC)C>ClCCl>[N+:11](=[CH:12][C:13]([O:27][CH2:26]/[CH:25]=[CH:24]/[C:23]1[C:18]([F:17])=[CH:19][C:20]([NH:29][C:30]([O:31][CH:32]([CH3:33])[CH3:34])=[O:35])=[CH:21][C:22]=1[F:28])=[O:14])=[N-:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 949N,N-DimethylanilineHCID 8471TriethylamineHCID 57296158Glyoxylyl Chloride p-toluenesulfonylhydrazoneHCID 58978084isopropyl 3,5-difluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

生成物 1

HCID 131726632(2e)-3-{2,6-Difluoro-4-[(isopropoxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

Glyoxylic acid chloride p-toluenesulfonylhydrazone (4.64 g, 17.8 mmol) was added to a suspension of isopropyl 3,5-difluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate (2.68 g, 9.89 mmol) in dichloromethane (66 mL). The mixture was cooled to 0° C. and treated with N,N-dimethylaniline (2.26 mL, 17.8 mmol). After 30 minutes, triethylamine (6.89 mL, 49.5 mmol) was added and the mixture stirred 30 minutes at 0° C. and 15 minutes at room temperature. The reaction mixture was then concentrated to ca. 15 mL and 50 mL of water added. The mixture was extracted with two portions of diethyl ether and the combined organic solutions washed with saturated NaHCO3, brine, and dried (MgSO4), filtered and concentrated. Purification by column chromatography (0-25% ethyl acetate-hexane) provided the title compound a yellow solid.

後処理

  1. concentrationThe reaction mixture was then concentrated to ca. 15 mL and 50 mL of water
  2. additionadded
  3. extractionThe mixture was extracted with two portions of diethyl ether
  4. washthe combined organic solutions washed with saturated NaHCO3, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography (0-25% ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-17a464035f7b48108458ace76583064d
出典データセット
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07279494B2

反応ノート

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