N,N-Dimethylaniline → (2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)prop-2-enyl diazoacetate

HRID 1179486ノート

反応式

HRID 1179486 の反応式
C1(C)C=CC(S([NH:10][N:11]=[CH:12][C:13](Cl)=[O:14])(=O)=O)=CC=1.[OH:17][CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:23][CH:22]=1.CN(C)C1C=CC=CC=1.C(N(CC)CC)C>ClCCl>[N+:11](=[CH:12][C:13]([O:17][CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:37])=[CH:23][CH:22]=1)=[O:14])=[N-:10]

参加物

6

反応物 4

HCID 949N,N-DimethylanilineHCID 8471TriethylamineHCID 57296158Glyoxylyl Chloride p-toluenesulfonylhydrazoneHCID 58978090benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

生成物 1

HCID 86619689(2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)prop-2-enyl diazoacetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Glyoxylic acid chloride p-toluenesulfonylhydrazone (1.66 g, 6.35 mmol) was added to a suspension of benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate (1.0 g, 3.53 mmol) in dichloromethane (25 mL). The mixture was cooled to 0° C. and treated with N,N-dimethylaniline (0.8 mL, 6.35 mmol). After 0.5 h, triethylamine (2.5 mL, 17.6 mmol) was added and the mixture stirred 2 h at 0° C. and warmed to room temperature. The reaction mixture was then concentrated and water was 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 silica gel column chromatography (gradient 0-25% EtOAc-hexane) provided the title compound.

後処理

  1. temperaturewarmed to room temperature
  2. concentrationThe reaction mixture was then concentrated
  3. additionwater was added
  4. extractionThe mixture was extracted with two portions of diethyl ether
  5. washthe combined organic solutions washed with saturated NaHCO3, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel column chromatography (gradient 0-25% EtOAc-hexane)

出典と根拠

ORDレコード
ord-8755f2912bf2400c8de5c9157b9396ab
出典データセット
uspto-grants-2007_10
特許番号
US07279494B2

反応ノート

読み込み中…