Hydrochloric Acid → HCID 178479444, compound

HRID 1720993Notes

Reaction equation

HRID 1720993 reaction equation
[ClH:1].Cl.C([O:7][CH:8](OCCCC)[C@H:9]([CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:42])[NH2:41])[NH:10][C:11](=[O:35])[C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:34])[C@@H:18]1[CH2:22][CH2:21][C:20](=[O:23])[N:19]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])CCC.[OH-].[Na+]>C(#N)C>[ClH:1].[CH2:27]([O:26][C:24]([N:19]1[C:20](=[O:23])[CH2:21][CH2:22][C@H:18]1[C:17]([N:13]1[CH2:14][CH2:15][CH2:16][C@H:12]1[C:11]([NH:10][C@H:9]([CH:8]=[O:7])[CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:41])[NH2:42])=[O:35])=[O:34])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178450974HCID 178450974, compound

Product 1

HCID 178479444HCID 178479444, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After 1N hydrochloric acid aqueous solution (30 ml) was added to a solution of N-benzyloxycarbonyl-L-pyroglutamyl-L-prolyl-L-argininal dibutylacetal hydrochloride (0.40 g, 0.60 mmol) in acetonitrile (60 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 0.26 g (80%) of N-benzyloxycarbonyl-L-pyroglutamyl-L-prolyl-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-8a2f1183ab53475fa9b28af59c4043a9
Source dataset
uspto-grants-1996_04
Patent number
US05508385

Reaction notes

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