Hydrochloric Acid → HCID 15593177, compound

HRID 2108180Notes

Reaction equation

HRID 2108180 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C@@H:4]([CH2:6][C:7]1[N:11]=[CH:10][NH:9][CH:8]=1)[NH2:5].N1C=CC=CC=1.CO.[C:21](=O)=[O:22].Cl>C(Cl)(Cl)Cl.CCOCC.CCCCCC>[CH3:1][O:2][C:3]([C@@H:4]1[NH:5][C:21](=[O:22])[N:11]2[CH:10]=[N:9][CH:8]=[C:7]2[CH2:6]1)=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 21973728Carbon dioxide methanolHCID 178501496HCID 178501496, compound

Product 1

HCID 15593177HCID 15593177, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21584099Diethylether hexaneSolvent

Procedure

1.7 g (10 mmol) of D-histidine methyl ester and 1.58 g (20 mmol, 1.61 ml) of distilled pyridine are dissolved in 50 ml of absolute chloroform, cooled to -40° to -50° C. with methanol/dry ice, and, at this temperature, a weak stream of HCl-free phosgene is introduced for 15 minutes. The mixture is stirred for 15 minutes in the cold state and poured into 200 ml of cold ether/hexane (2:1). A white, deliquescent precipitate is obtained which is quickly suctioned off and washed with ether. The precipitate is taken up in 100 ml of 1N Na2CO3 solution and extracted six times with chloroform. After drying of the organic phase over sodium sulfate, the solvent is removed by evaporation; any present traces of pyridine are removed under a high vacuum. The compound is crystallized from methanol.

Workup

  1. customA white, deliquescent precipitate is obtained which
  2. washwashed with ether
  3. extractionextracted six times with chloroform
  4. dry with materialAfter drying of the organic phase over sodium sulfate
  5. customthe solvent is removed by evaporation
  6. customany present traces of pyridine are removed under a high vacuum
  7. customThe compound is crystallized from methanol

Sources & evidence

ORD record
ord-1af8a3f274024ceaa47647aa11538ba4
Source dataset
uspto-grants-1990_06
Patent number
US04937352

Reaction notes

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