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

HRID 1179486노트

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HRID 1179486 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8755f2912bf2400c8de5c9157b9396ab
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279494B2

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