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(2,4-Dichlorophenoxy)Acetic Acid → 3-{3-[2-(2,4-Dichlorophenoxy)acetylamino]-4-methoxyphenyl}-2-isopropoxypropanoic acid

HRID 1985407
ノート
印刷プレビュー

反応式

HRID 1985407 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([O:17][CH:18]([CH3:20])[CH3:19])[C:12]([O:14]CC)=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Cl:21][C:22]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:23]=1[O:24][CH2:25][C:26](O)=[O:27].C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C>O1CCCC1>[Cl:21][C:22]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:23]=1[O:24][CH2:25][C:26]([NH:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([O:17][CH:18]([CH3:19])[CH3:20])[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9])=[O:27]
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 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 22494286Ethyl 3-(3-amino-4-methoxyphenyl)-2-isopropoxypropanoate

生成物 1

HCID 577195233-{3-[2-(2,4-Dichlorophenoxy)acetylamino]-4-methoxyphenyl}-2-isopropoxypropanoic acid収率 8.2%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
50 °C

実験手順

30 mg of Ethyl 3-(3-amino-4-methoxyphenyl)-2-isopropoxypropanoate and 20 mg of 2,4-dichlorophenoxyacetic acid were dissolved in 0.5 ml of tetrahydrofuran, and 30 mg of carbonyldiimidazole and 0.05 ml of triethylamine were added, and the mixture was stirred at 50° C. for 4 hours. The reaction mixture was then partitioned between water and ethyl acetate, and the organic layer was concentrated. The residue was dissolved in 0.6 ml of ethanol, and 0.12 ml of 5N sodium hydroxide was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was neutralized with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by HPLC using a reverse-phase column and a water-acetonitrile-trifluoroacetic acid elution solvent, to give 3.4 mg of the title compound.

後処理

  1. customThe reaction mixture was then partitioned between water and ethyl acetate
  2. concentrationthe organic layer was concentrated
  3. dissolutionThe residue was dissolved in 0.6 ml of ethanol
  4. addition0.12 ml of 5N sodium hydroxide was added
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. extractionextracted with ethyl acetate
  7. concentrationThe organic layer was concentrated
  8. customthe residue was purified by HPLC
  9. washa water-acetonitrile-trifluoroacetic acid elution solvent

出典と根拠

ORDレコード
ord-732e35fd889f415092ab96ba38c09a7f
出典データセット
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07544835B2

反応ノート

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