苯甲酰氯 → tetraethyl N-benzoyl-5-aminopentane-1,1-bisphosphonate

HRID 1974

反应方程式

HRID 1974 反应方程式
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([P:24]([O:29][CH2:30][CH3:31])(=[O:28])[O:25][CH2:26][CH3:27])[P:16]([O:21][CH2:22][CH3:23])(=[O:20])[O:17][CH2:18][CH3:19].C(N(CC)CC)C>ClCCl>[C:1]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([P:24]([O:29][CH2:30][CH3:31])(=[O:28])[O:25][CH2:26][CH3:27])[P:16]([O:21][CH2:22][CH3:23])(=[O:20])[O:17][CH2:18][CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参与物

5

反应物 3

HCID 7412苯甲酰氯HCID 8471三乙胺HCID 12102991Tetraethyl 5-aminopentane-1,1-bisphosphonate

产物 1

HCID 19689031tetraethyl N-benzoyl-5-aminopentane-1,1-bisphosphonate收率 30.7%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂2 次

实验过程

A solution of benzoyl chloride (0.73 g, 5.0 mmol) in dichloromethane was added slowly to a solution of tetraethyl 5-aminopentane-1,1-bisphosphonate (1.50 g, 4.5 mmol) from Example 11, part A, and triethylamine (0.76 mL, 5.5 mmol) in dichloromethane at 0° C. After warming to room temperature for 30 minutes, the reaction was quenched by addition of 1N HCl (30 mL). The product was extracted into dichloromethane (2×20 mL) and the combined organic layers were washed with saturated NaHCO3 (2×15 mL), dried (Na2SO4), and concentrated in vacuo. Flash chromatography on silica gel eluting with 15% i-propanol in ethylacetate in EtOAc gave the title compound (0.64 g) as an oil.

后处理

  1. customthe reaction was quenched by addition of 1N HCl (30 mL)
  2. extractionThe product was extracted into dichloromethane (2×20 mL)
  3. washthe combined organic layers were washed with saturated NaHCO3 (2×15 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-18119a89941c4368a7ad288ebe54d59f
来源数据集
uspto-grants-1998_03
专利号
US05728650

关联笔记

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