海萝胶 → 3-(Butylamino)propane-1,1-bisphosphonic acid

HRID 1973

反应方程式

HRID 1973 反应方程式
[CH2:1]([NH:5][C:6](=O)[CH2:7][CH:8]([P:17]([O:22]CC)([O:19]CC)=[O:18])[P:9]([O:14]CC)([O:11]CC)=[O:10])[CH2:2][CH2:3][CH3:4].B.CSC.Cl>C1COCC1>[CH2:1]([NH:5][CH2:6][CH2:7][CH:8]([P:17]([OH:22])(=[O:18])[OH:19])[P:9]([OH:14])(=[O:10])[OH:11])[CH2:2][CH2:3][CH3:4]

参与物

5

反应物 3

HCID 313海萝胶HCID 12423031(Dimethyl sulfide)trihydroboronHCID 19689044N-butyl-3,3-bis(diethoxyphosphinyl)propionamide

产物 1

HCID 196890223-(Butylamino)propane-1,1-bisphosphonic acid收率 109%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
0 °C

实验过程

A solution of N-butyl-3,3-bis(diethoxyphosphinyl)propionamide (1.40 g, 3.5 mmol) in THF (9 mL) was cooled to 0° C., and borane-methyl sulfide (0.90 ml, 9.0 mmol) was added via syringe. The reaction was stirred at 0° C. for 5 minutes, then warmed to 65° C. for 3 hours. The reaction mixture was cooled to 0° C. and 6N HCl (6 ml) was added carefully. The solvent was removed in vacuo, and the residue was repeatedly concentrated from methanol (3×10 mL). The product was dissolved in 12N HCl and heated at reflux for 20 hours. After cooling, the volatile materials were removed under vacuum, the residue was dissolved in water (10 mL) and then concentrated to give 1.05 g of Compound No. 158 as a hygroscopic glass.

后处理

  1. temperaturewarmed to 65° C. for 3 hours
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customThe solvent was removed in vacuo
  4. concentrationthe residue was repeatedly concentrated from methanol (3×10 mL)
  5. dissolutionThe product was dissolved in 12N HCl
  6. temperatureheated
  7. temperatureat reflux for 20 hours
  8. temperatureAfter cooling
  9. customthe volatile materials were removed under vacuum
  10. dissolutionthe residue was dissolved in water (10 mL)
  11. concentrationconcentrated

来源与证据

ORD记录
ord-3f7c12ece3d5427682be4ea183c9152d
来源数据集
uspto-grants-1998_03
专利号
US05728650

关联笔记

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