2-Iodobenzoic acid → (2-Iodobenzoylamino)-(2-iodophenyl)-acetic Acid Methyl Ester

HRID 660571노트

반응식

HRID 660571 반응식
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C.[CH3:40][O:41][C:42](=[O:52])[CH:43]([NH2:51])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[I:50]>C1COCC1>[CH3:40][O:41][C:42](=[O:52])[CH:43]([NH:51][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[I:1])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[I:50]

참가 물질

7

반응물 5

HCID 69412-Iodobenzoic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68840368Methyl 2-amino-2-(2-iodophenyl)acetate

생성물 1

HCID 68839341(2-Iodobenzoylamino)-(2-iodophenyl)-acetic Acid Methyl Ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-iodobenzoic acid (6.4 g, 25.8 mmol) in THF (90 mL) is added HOBt (3.5 g, 25.8 mmol). After the mixture is stirred at RT for 10 min, EDCl (4.93 g, 25.8 mmol) is added followed by triethylamine (4.9 mL, 34.4 mmol). The mixture is stirred at RT for 40 min then amino-(2-iodophenyl)-acetic acid methyl ester (5.0 g, 17.2 mmol) is added and stirring is continued for 18 h. The solvent is removed under reduced pressure and water is added to the residue. The mixture is extracted with EtOAc and the organic phase is washed with brine and dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 0-60% EtOAc/hexane as eluent to give the title compound.

후처리

  1. stirringThe mixture is stirred at RT for 40 min
  2. stirringstirring
  3. waitis continued for 18 h
  4. customThe solvent is removed under reduced pressure and water
  5. additionis added to the residue
  6. extractionThe mixture is extracted with EtOAc
  7. washthe organic phase is washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent is removed under reduced pressure
  10. customthe residue purified by flash chromatography

출처 및 근거

ORD 기록
ord-45843441750b4de891869517c6bbf880
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084448B2

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