Hydrochloric Acid → HCID 178479450, compound

HRID 1720999Notes

Reaction equation

HRID 1720999 reaction equation
[ClH:1].C([O:6][CH:7](OCCCC)[C@H:8]([CH2:32][CH2:33][CH2:34][NH:35][C:36](=[NH:38])[NH2:37])[NH:9][C:10](=[O:31])[CH2:11][NH:12][C:13](=[O:30])[C@@H:14]1[CH2:18][CH2:17][C:16](=[O:19])[N:15]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])CCC.Cl.[OH-].[Na+]>C(#N)C>[ClH:1].[CH2:23]([O:22][C:20]([N:15]1[C:16](=[O:19])[CH2:17][CH2:18][C@H:14]1[C:13]([NH:12][CH2:11][C:10]([NH:9][C@H:8]([CH:7]=[O:6])[CH2:32][CH2:33][CH2:34][NH:35][C:36](=[NH:37])[NH2:38])=[O:31])=[O:30])=[O:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178450991HCID 178450991, compound

Product 1

HCID 178479450HCID 178479450, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-pyroglutamyl-glycyl-L-argininal dibutylacetal hydrochloride (30 mg, 0.048 mmol) in acetonitrile (4.8 ml) was added 1N hydrochloric acid aqueous solution (2.4 ml). The mixture was reacted at 36° C. for an hour with stirring. After completion of the reaction, pH of the reaction mixture was adjusted to 4.8 with 1N sodium hydroxide aqueous solution. The solvent was distilled off under reduced pressure and chloroform was added to the residue. Insoluble matters were removed by filtration. After the filtrate was concentrated, the residue was recrystallized from chloroform-hexane to give 15.7 mg (66%) of N-benzyloxycarbonyl-L-pyroglutamyl-glycyl-L-argininal hydrochloride.

Workup

  1. customThe mixture was reacted at 36° C. for an hour
  2. customAfter completion of the reaction, pH of the reaction mixture
  3. distillationThe solvent was distilled off under reduced pressure and chloroform
  4. additionwas added to the residue
  5. customInsoluble matters were removed by filtration
  6. concentrationAfter the filtrate was concentrated
  7. customthe residue was recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-a96a859fd73a4701b95f139bfd106f33
Source dataset
uspto-grants-1996_04
Patent number
US05508385

Reaction notes

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