Potassium Carbonate → HCID 178476193, compound

HRID 1834211Notes

Reaction equation

HRID 1834211 reaction equation
[CH2:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:19])[C@H:10]([CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:18])[NH2:17])[NH2:11])[CH2:5][CH2:4]1)[CH3:2].C(=O)([O-])[O-:21].[K+].[K+].[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][C:37]=1[O:38][CH3:39])[CH:34]=[C:33]([S:40](Cl)(=[O:42])=[O:41])[CH:32]=[CH:31]2>O.O1CCOCC1>[C:9]([OH:19])(=[O:21])[CH3:10].[CH2:1]([CH:3]1[CH2:4][CH2:5][N:6]([C:9](=[O:19])[C@H:10]([CH2:12][CH2:13][CH2:14][NH:15][C:16](=[NH:17])[NH2:18])[NH:11][S:40]([C:33]2[CH:32]=[CH:31][C:30]3[C:35](=[CH:36][C:37]([O:38][CH3:39])=[C:28]([O:27][CH3:26])[CH:29]=3)[CH:34]=2)(=[O:42])=[O:41])[CH2:7][CH2:8]1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 144577546,7-Dimethoxynaphthalene-2-sulfonyl chlorideHCID 178436821HCID 178436821, compound

Product 1

HCID 178476193HCID 178476193, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 1.00 g (0.0037 mole) of 4-ethyl-1-(L-arginyl) piperidine and 0.61 g (0.0044 mole) of potassium carbonate in 10 ml of water, which had been cooled to 0° C, was added dropwise a solution of 1.25 g (0.0044 mole) of 6,7-dimethoxy-2-naphthalenesulfonyl chloride in 30 ml of dioxane with vigorous stirring over a period of 30 minutes. The reaction mixture was stirred for additional 5 hours at room temperature and the formed precipitate was removed by filtration. The solvent was evaporated under reduced pressure, and to the residue was added 50 ml of chloroform. The undissolved material was filtered off and the solution was dried over sodium sulfate. Addition of 10 ml of acetic acid to this solution followed by evaporation of the solvent gave a viscous oily product, which was reprecipitated with methanol-ethyl ether to afford 4-ethyl-1-[N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl]piperidine acetate in a 62% yield.

Workup

  1. stirringThe reaction mixture was stirred for additional 5 hours at room temperature
  2. customthe formed precipitate was removed by filtration
  3. customThe solvent was evaporated under reduced pressure
  4. additionto the residue was added 50 ml of chloroform
  5. filtrationThe undissolved material was filtered off
  6. dry with materialthe solution was dried over sodium sulfate
  7. additionAddition of 10 ml of acetic acid to this solution
  8. customfollowed by evaporation of the solvent
  9. customgave a viscous oily product, which
  10. customwas reprecipitated with methanol-ethyl ether

Sources & evidence

ORD record
ord-f3cfacaaaeed4e5792e07d227fc12f71
Source dataset
uspto-grants-1978_01
Patent number
US04069323

Reaction notes

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