Hydrochloric Acid → HCID 178462137, compound

HRID 1720995Notes

Reaction equation

HRID 1720995 reaction equation
[ClH:1].C([O:6][CH:7](OCCCC)[C@H:8]([CH2:33][CH2:34][CH2:35][NH:36][C:37](=[NH:39])[NH2:38])[NH:9][C:10](=[O:32])[C@H:11]([CH3:31])[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][C@H:11]([C:10]([NH:9][C@H:8]([CH:7]=[O:6])[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[NH:38])[NH2:39])=[O:32])[CH3:31])=[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 178450984HCID 178450984, compound

Product 1

HCID 178462137HCID 178462137, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-pyroglutamyl-L-alanyl-L-argininal dibutylacetal hydrochloride (0.22 g, 0.35 mmol) in acetonitrile (35 ml) was added 1N hydrochloric acid aqueous solution (17.5 ml). The mixture was reacted at 36° C. for 1.5 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-methanol (20:1) 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 0.10 g (57%) of N-benzyloxycarbonyl-L-pyroglutamyl-L-alanyl-L-argininal hydrochloride.

Workup

  1. customThe mixture was reacted at 36° C. for 1.5 hour
  2. customAfter completion of the reaction, pH of the reaction mixture
  3. distillationThe solvent was distilled off under reduced pressure and chloroform-methanol (20:1)
  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-ac46927cdad74c46aa1a4011705da41d
Source dataset
uspto-grants-1996_04
Patent number
US05508385

Reaction notes

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