碳酸氢钠 → Methyl 4-acetylamino-5-bromo-3-iodosalicylate

HRID 17538笔记

反应方程式

HRID 17538 反应方程式
[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]

参与物

6

反应物 3

HCID 516892碳酸氢钠HCID 56924451Trimethylbenzylammonium DichloroiodateHCID 68586212Methyl 4-acetamido-5-bromo-2-hydroxybenzoate

产物 1

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

试剂、催化剂与溶剂 2

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂HCID 6344二氯甲烷溶剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-9e819f94cbef4ecca05582838049e421
来源数据集
uspto-grants-2010_06
专利号
US07737166B2

反应笔记

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