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1,1'-Carbonyldiimidazole → 2-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-(2-isopropoxy-3-methoxybenzyl)acetamide

HRID 1666311
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HRID 1666311 반응식
[C:1]([O:4][CH:5]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1)[C:6]([OH:8])=O)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:33]([O:36][C:37]1[C:45]([O:46][CH3:47])=[CH:44][CH:43]=[CH:42][C:38]=1[CH2:39][NH:40][CH3:41])([CH3:35])[CH3:34]>ClCCl>[CH3:20][O:19][C:11]1[CH:10]=[C:9]([CH:5]([O:4][C:1](=[O:3])[CH3:2])[C:6]([N:40]([CH3:41])[CH2:39][C:38]2[CH:42]=[CH:43][CH:44]=[C:45]([O:46][CH3:47])[C:37]=2[O:36][CH:33]([CH3:34])[CH3:35])=[O:8])[CH:14]=[C:13]([O:15][CH3:16])[C:12]=1[O:17][CH3:18]
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참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 433884002-Isopropoxy-3-methoxy-benzyl-methylamineHCID 67081678alpha-Acetoxy-3,4,5-trimethoxyphenyl-acetic acid

생성물 1

HCID 670818692-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-(2-isopropoxy-3-methoxybenzyl)acetamide수율 98.1%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
2회

실험 절차

A solution of α-acetoxy-3,4,5-trimethoxyphenyl-acetic acid (5.0 g) in dichloromethane (40 ml) was reacted with 1,1′-carbonyldiimidazole (2.92 g) at room temperature for 30 minutes. The solution was refluxed for 30 minutes, after which 2-isopropoxy-3-methoxy-N-methylbenzylamine (3.26 g) dissolved in dichloromethane (10 ml) was added. The mixture was stirred at room temperature for 2 hours, after which it was washed with aqueous hydrochloric acid (20 ml, is 1M) followed by aqueous sodium hydrogen carbonate (20 ml, 0.5 M). The organic phase was dried and concentrated to dryness, leaving crude 2-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-(2-isopropoxy-3-methoxybenzyl)acetamide (7.27 g).

후처리

  1. temperatureThe solution was refluxed for 30 minutes
  2. additionwas added
  3. washafter which it was washed with aqueous hydrochloric acid (20 ml, is 1M)
  4. customThe organic phase was dried
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-2f81bc0b02fb4639ae46d714207c3d6e
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044067B2

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