Hydrochloric Acid → HCID 178512166, compound

HRID 2293060Notes

Reaction equation

HRID 2293060 reaction equation
[NH2:1][C@H:2]([C:13]([OH:15])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:12])[NH:8][N+:9]([O-:11])=[O:10].C(=O)(O)[O-].[Na+].[N:21]([CH2:24][C:25]([O:27]CC)=[O:26])=[C:22]=[O:23].Cl>O>[N+:9]([NH:8][C:7](=[NH:12])[NH:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[NH:1][C:22](=[O:23])[N:21]([CH2:24][C:25]([OH:27])=[O:26])[C:13]1=[O:15])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76283Ethyl isocyanatoacetateHCID 516892Sodium BicarbonateHCID 178512188HCID 178512188, compound

Product 1

HCID 178512166HCID 178512166, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

11 g (0.05 mol) of H-Arg(NO2)-OH are dissolved with 4.3 g (0.05 mol) of sodium bicarbonate in 200 ml of water under reflux. At 70° C., 7.1 g (0.055 mol) of ethyl isocyanato-acetate are added dropwise. The mixture is stirred at 70° C. for 1 hour, left to cool and stirred at room temperature overnight, 50 ml of concentrated hydrochloric acid are added, the mixture is concentrated, 20 ml of 50% concentrated hydrochloric acid are added, the mixture is heated under reflux for 1 hour and substantially concentrated, and the precipitated product is filtered off with suction.

Workup

  1. temperatureunder reflux
  2. waitleft
  3. temperatureto cool
  4. stirringstirred at room temperature overnight
  5. concentrationthe mixture is concentrated
  6. addition20 ml of 50% concentrated hydrochloric acid are added
  7. temperaturethe mixture is heated
  8. temperatureunder reflux for 1 hour
  9. concentrationsubstantially concentrated
  10. filtrationthe precipitated product is filtered off with suction

Sources & evidence

ORD record
ord-24171b99e8494540bb2cd38a5511c7fb
Source dataset
uspto-grants-1997_11
Patent number
US05686421

Reaction notes

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