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

HRID 863

反应方程式

HRID 863 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 mmole) 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 (Na2 SO4), 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. customThe combined organic layer was dried (Na2 SO4)
  7. filtrationfiltered
  8. customevaporated

来源与证据

ORD记录
ord-50d2591cf07947e7ab725904f4df96f4
来源数据集
uspto-grants-1998_03
专利号
US05723444

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