Hydrochloric Acid → HCID 3080936, compound

HRID 851526Notes

Reaction equation

HRID 851526 reaction equation
[Na].[NH2:2][C@H:3]([C:9]([O-:11])=[O:10])[CH2:4][CH2:5][C:6]([O-:8])=[O:7].[NH2:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14].Cl.C(N=C=NCCCN(C)C)C.Cl>O>[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][C:6]([OH:8])=[O:7].[NH2:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5360545SodiumHCID 86738878HCID 86738878, compound

Product 1

HCID 3080936HCID 3080936, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

450 mg of the polymer mainly comprising sodium of L-glutamate/L-alanine copolymer obtained in Example 3 was dissolved in 10 ml of water, to which an aqueous solution prepared by dissolving 66.3 mg of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC, condensing agent) in 5 ml of water was added. An aqueous solution prepared by dissolving 88.5 mg of P-[bis(2-chloroethyl)amino]L-phenylalanine (melphalan), which is a publicly known anti-cancer drug, in 20 ml of water was added dropwise to the mixed solution in 10 minutes. This reaction solution was stirred overnight at room temperature. When hydrochloric acid was added to the reaction solution to adjust the pH to 4.0, a white precipitate appeared. The precipitate was isolated by centrifugation and was washed with dilute hydrochloric acid. Thus obtained white solid was dissolved in 20 ml of 0.1 N caustic soda solution and dialyzed against pure water at 4° C. for 3 days on a permeable cellophane tube. The dialyzate was lyophilized to give 484 mg of L-glutamic acid/L-alanine copolymer sodium salt-melphalan conjugate as a curdy solid.

Workup

  1. customprepared
  2. additionwas added
  3. customAn aqueous solution prepared
  4. customThe precipitate was isolated by centrifugation
  5. washwas washed with dilute hydrochloric acid
  6. dissolutionThus obtained white solid was dissolved in 20 ml of 0.1 N caustic soda solution
  7. customdialyzed against pure water at 4° C. for 3 days on a permeable cellophane tube

Sources & evidence

ORD record
ord-33f2dc1d01bc4851907f2c467c4ca089
Source dataset
uspto-grants-1983_05
Patent number
US04385169

Reaction notes

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