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

HRID 863

反応式

HRID 863 の反応式
[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

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 140379085benzyl N-[3-(hydroxymethyl)pyrrolidine-1-carboximidoyl]carbamate

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 21899848Ethylacetate heptane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-50d2591cf07947e7ab725904f4df96f4
出典データセット
uspto-grants-1998_03
特許番号
US05723444

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