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

HRID 1985407
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HRID 1985407 반응식
[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]
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참가 물질

6

반응물 4

HCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 22494286Ethyl 3-(3-amino-4-methoxyphenyl)-2-isopropoxypropanoate

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-732e35fd889f415092ab96ba38c09a7f
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07544835B2

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