Methanol → HCID 178484885, compound

HRID 274218

Reaction equation

HRID 274218 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][NH:6][C@H:7]([C:15]([OH:17])=[O:16])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:14])[NH2:13].[CH3:18]O>>[ClH:3].[ClH:3].[CH3:18][O:16][C:15](=[O:17])[C@H:7]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:13])[NH2:14])[NH:6][CH3:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 178484884HCID 178484884, compound

Product 1

HCID 178484885HCID 178484885, compound

Conditions

Temperature
40 °C

Procedure

6.4 ml of thionyl chloride are added dropwise to a suspension of 15.06 g of N-methylarginine in 50 ml of absolute methanol at -10° C. The mixture is then allowed to come to room temperature, while stirring. Since starting material is still present after a reaction time of 17 hours, a further 9.6 ml of thionyl chloride are added in portions, the mixture is heated at 40° C. for 4 hours, the insoluble material is filtered off with suction and the filtrate is concentrated. The oily residue is dissolved in water, the insoluble material is filtered off and the product is freeze-dried.

Workup

  1. customto come to room temperature
  2. customafter a reaction time of 17 hours
  3. filtrationthe insoluble material is filtered off with suction
  4. concentrationthe filtrate is concentrated
  5. dissolutionThe oily residue is dissolved in water
  6. filtrationthe insoluble material is filtered off
  7. customthe product is freeze-dried

Sources & evidence

ORD record
ord-b37a7ab4c7a04dd1a6fb0a747db9b236
Source dataset
uspto-grants-1995_02
Patent number
US05389614

Linked notes

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