Hydrochloric Acid → HCID 178419078, compound

HRID 1731194Notes

Reaction equation

HRID 1731194 reaction equation
NCC([NH:5][C@H:6]([C:13]([OH:15])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=O.C(SC(=N)N)C.OS(O)(=O)=O.[NH2:27]CC(N[C@H](C(O)=O)CC1N=CNC=1)=O.Cl.[OH-:43].[Na+].C(C(O)(C([O-])=O)CC([O-])=O)C([O-])=O.C(C(O)(C([O-])=O)CC([O-])=O)C([O-])=O.[OH2:71].[Na+].[Na+].[Na+].[K+].[K+].[K+].C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O.N(CC(N[C@H](C(O)=O)CC1N=CNC=1)=O)C(N)=N.Cl>O.N1C=CC=CC=1>[NH:12]([CH2:8][C:9]([OH:71])=[O:43])[C:11]([NH2:10])=[NH:27].[NH2:5][C@H:6]([C:13]([OH:15])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1

Participants

13

Reactant 9

HCID 313Hydrochloric AcidHCID 1118Sulfuric Acid2×HCID 5139S-Ethylisothiourea2×HCID 10236NinhydrinHCID 14798Sodium HydroxideHCID 171403Sodium citrate, potassium citrate, citric acidHCID 178479243HCID 178479243, compoundHCID 178511447HCID 178511447, compoundHCID 178513020HCID 178513020, compound

Product 2

HCID 178419078HCID 178419078, compoundHCID 178513022HCID 178513022, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent4×HCID 1049PyridineSolvent4×

Procedure

H2O (n=1) was prepared from glycyl-L-histidine and S-ethylisothiourea.H2SO4. Solutions of 1.50 g. of S-ethylisothiourea.H2SO4 in 5 ml of H2O and 1.74 g. of Gly-His.HCl in 3 ml of H2O were adjusted to pH 8-9 with 4 N NaOH. They were then mixed and kept at room temperature for a week. The cloudy suspension was filtered and the filtrate concentrated to dryness in vacuo. The residue, after addition of a small amount of EtOH, was dried in vacuo. A small amount of H2O was added to dissolve the dry residue and resulting solution was poured onto the column (2.5 cm i.d. × 30 cm Amberlite CG-120, 200-400 mesh, pyridine form). H2O, 1.0 M pyridine, 2.0 M pyridine, and 1.0 M pyridine--0.5 M NH4OH were used as the effluent solutions. Each fraction was tested for ninhydrin, Pauli, and Sakaguchi reactions. The fractions containing guanidinoacetyl-L-histidine were pooled and concentrated to dryness in vacuo. Cryst from H2O--EtOH; yield, 69.2%; mp, 108-111° C., decomp. Hydrolysis (6 N HCl, 110° , 24 hours.) gave guanidinoacetic acid and histidine, as confirmed be tlc. (thin layer chromatography).

Workup

  1. additionThey were then mixed
  2. waitkept at room temperature for a week
  3. filtrationThe cloudy suspension was filtered
  4. concentrationthe filtrate concentrated to dryness in vacuo
  5. additionThe residue, after addition of a small amount of EtOH
  6. customwas dried in vacuo
  7. additionA small amount of H2O was added
  8. dissolutionto dissolve the dry residue
  9. customresulting solution
  10. concentrationconcentrated to dryness in vacuo
  11. customyield

Sources & evidence

ORD record
ord-f481a805934f4387a2abd702b14ad33c
Source dataset
uspto-grants-1976_11
Patent number
US03995051

Reaction notes

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