三乙胺 → [1-(N-phenylmethoxycarbonylcarbamimidoyl)pyrrolidin-3-yl]methyl methanesulfonate

HRID 1450707

反应方程式

HRID 1450707 反应方程式
[CH2:1]([O:8][C:9]([NH:11][C:12]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:19][OH:20])[CH2:15]1)=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(OCC)(=O)C.CCCCCCC.C(OCC)C>[CH2:1]([O:8][C:9]([NH:11][C:12]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:19][O:20][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:15]1)=[NH:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参与物

6

反应物 3

HCID 8471三乙胺HCID 31297甲基磺酰氯HCID 140379085benzyl N-[3-(hydroxymethyl)pyrrolidine-1-carboximidoyl]carbamate

产物 1

HCID 140379087[1-(N-phenylmethoxycarbonylcarbamimidoyl)pyrrolidin-3-yl]methyl methanesulfonate收率 50%

试剂、催化剂与溶剂 2

HCID 3283乙醚溶剂HCID 21899848Ethylacetate heptane溶剂

反应条件

温度
0 °C

实验过程

0.7 g (2.53 mmole) (3RS)-1-(N-benzyloxycarbonylamidino)-3-hydroxymethyl pyrrolidine and 0.70 ml (5.05 mmole) triethylamine was dissolved in 15 ml diethyl ether/CH2Cl2 1/1 and the mixture was cooled to 0° C. 0.25 ml (3.29 mole) methanesulphonyl chloride in 3 ml diethyl ether was slowly added and the reaction mixture was stirred at 0° C. for three hours. The solvent was evaporated and the residue was dissolved in ethyl acetate and extracted with a 0.3M KHSO4 -solution. The water layer was washed once with CH2Cl2. The water layer was made neutral with 10M NaOH-solution and extracted twice with CH2Cl2. The combined organic layer was dried (Na2SO4), filtered and evaporated to yield 0.450 g (50%) of the title compound.

后处理

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionextracted with a 0.3M KHSO4 -solution
  4. washThe water layer was washed once with CH2Cl2
  5. extractionextracted twice with CH2Cl2
  6. dry with materialThe combined organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

来源与证据

ORD记录
ord-58ec3d486e2e4d078565793b5fc131a0
来源数据集
uspto-grants-1997_02
专利号
US05602253

关联笔记

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