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

HRID 1610805Notes

Reaction equation

HRID 1610805 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
0 °C

Procedure

0.7 g (2.53 mmole) (3RS)-1-(N-benzyloxycarbonylamidino)-3-hydroxymethylpyrrolidine 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 0.3 M 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.

Workup

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

Sources & evidence

ORD record
ord-102e0f0bef734b468de9c4b6b67e4a26
Source dataset
uspto-grants-2006_01
Patent number
US06984627B1

Reaction notes

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