Hydrochloric Acid → HCID 178462138, compound

HRID 1721003Notes

Reaction equation

HRID 1721003 reaction equation
[ClH:1].Cl.C([O:7][CH:8](OCCCC)[C@H:9]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:40])[NH2:39])[NH:10][C:11](=[O:33])[C@H:12]([CH3:32])[NH:13][C:14](=[O:31])[C@H:15]1[CH2:19][CH2:18][C:17](=[O:20])[N:16]1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])CCC.[OH-].[Na+]>C(#N)C>[ClH:1].[CH2:24]([O:23][C:21]([N:16]1[C:17](=[O:20])[CH2:18][CH2:19][C@@H:15]1[C:14]([NH:13][C@H:12]([C:11]([NH:10][C@H:9]([CH:8]=[O:7])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:40])=[O:33])[CH3:32])=[O:31])=[O:22])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178450985HCID 178450985, compound

Product 1

HCID 178462138HCID 178462138, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After 1N hydrochloric acid aqueous solution (22 ml) was added to a solution of N-benzyloxycarbonyl-D-pyroglutamyl-L-alanyl-L-argininal dibutylacetal hydrochloride (0.28 g, 0.44 mmol) in acetonitrile (44 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 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 0.19 g (86%) of N-benzyloxycarbonyl-D-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
  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-14638742a0c341959b530b6ec296b91f
Source dataset
uspto-grants-1996_04
Patent number
US05508385

Reaction notes

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