Sulfuric Acid → HCID 178512838, compound

HRID 1721007Notes

Reaction equation

HRID 1721007 reaction equation
C([O:5][CH:6](OCCCC)[C@H:7]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:40])[NH2:39])[NH:8][C:9](=[O:33])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:32])[C@@H:16]1[CH2:20][CH2:19][C:18](=[O:21])[N:17]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])CCC.S(=O)(=O)(O)O.[OH-].[Na+]>C(#N)C>[CH2:25]([O:24][C:22]([N:17]1[C:18](=[O:21])[CH2:19][CH2:20][C@H:16]1[C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([NH:8][C@H:7]([CH:6]=[O:5])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:40])=[O:33])=[O:32])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 178450973HCID 178450973, compound

Product 1

HCID 178512838HCID 178512838, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-pyroglutamyl-L-prolyl-L-argininal dibutylacetal 1/2 sulfate (0.61 g, 0.90 mmol) in acetonitrile (90 ml) was added 1N sulfuric acid aqueous solution (45 ml). The mixture was reacted at 36° C. for 4 hours with stirring. After completion of the reaction, pH of the reaction mixture was adjusted to 5.6 with 1N sodium hydroxide aqueous solution. The solvent was distilled off under reduced pressure and chloroform was added to the residue. Insoluble matters were filtered off. After the filtrate was concentrated, the residue was recrystallized from chloroform-hexane to give 0.43 g (87%) of N-benzyloxycarbonyl-L-pyroglutamyl-L-prolyl-L-argininal.1/2 sulfate.

Workup

  1. customThe mixture was reacted at 36° C. for 4 hours
  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. filtrationInsoluble matters were filtered off
  6. concentrationAfter the filtrate was concentrated
  7. customthe residue was recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-854aafb38c344a6ca2a94cd8d48f09f9
Source dataset
uspto-grants-1996_04
Patent number
US05508385

Reaction notes

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