Sodium Bicarbonate → Methyl 4-acetylamino-5-bromo-3-iodosalicylate

HRID 17538

반응식

HRID 17538 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:16])[C:8](=[CH:13][C:14]=1[Br:15])[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].[I:17](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO>[C:1]([NH:4][C:5]1[C:6]([I:17])=[C:7]([OH:16])[C:8](=[CH:13][C:14]=1[Br:15])[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 56924451Trimethylbenzylammonium DichloroiodateHCID 68586212Methyl 4-acetamido-5-bromo-2-hydroxybenzoate

생성물 1

HCID 86097515Methyl 4-acetylamino-5-bromo-3-iodosalicylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Methyl 4-acetylamino-5-bromosalicylate (I-249) (576 mg, 2.0 mmol) was dissolved in a mixed liquid of methylene chloride (20 ml) and methanol (10 ml), then benzyltrimethylammonium dichloroiodate (835 mg, 2.4 mmol) and sodium bicarbonate (1.1 g, 13.0 mmol) were added, followed by stirring at room temperature for 30 hours. The reaction liquid was filtered, the filtrate was concentrated under reduced pressure, then saturated ammonium chloride water was added to the residue, followed by extraction twice with chloroform, then the organic layer was washed with saturated sodium thiosulfate water, and dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with chloroform/methanol (50:1) gave the entitled compound (889 mg, quant.) as a pale yellow solid.

후처리

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionsaturated ammonium chloride water was added to the residue
  5. extractionfollowed by extraction twice with chloroform
  6. washthe organic layer was washed with saturated sodium thiosulfate water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration and concentration under reduced pressure
  9. customthe eluate with chloroform/methanol (50:1) gave the entitled compound (889 mg, quant.) as a pale yellow solid

출처 및 근거

ORD 기록
ord-9e819f94cbef4ecca05582838049e421
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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