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

HRID 341803

Reaktionsgleichung

Reaktionsgleichung von HRID 341803
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 21899848Ethylacetate heptaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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 (Na2SO4), filtered and evaporated to yield 0.450 g (50%) of the title compound.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6f16cde9dcb8417abd9c9d5d6c832f96
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856307

Verknüpfte Notizen

Wird geladen…