Hydrochloric Acid → HCID 178445997, compound

HRID 1578296Notes

Reaction equation

HRID 1578296 reaction equation
C[O:2][C:3](=[O:36])[C@H:4]([CH2:32][CH:33]([CH3:35])[CH3:34])[NH:5][C:6](=[O:31])[C@H:7]([CH2:25][C:26]1[N:30]=[CH:29][NH:28][CH:27]=1)[NH:8][C:9](=[O:24])[CH2:10][NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20]C(=O)C)=[CH:16][CH:15]=1)=[O:13].[OH-].[Na+].Cl.O>CO>[OH:20][C:17]1[CH:16]=[CH:15][C:14]([C:12](=[O:13])[NH:11][CH2:10][C:9]([NH:8][C@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:36])=[O:2])[CH2:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:25][C:26]2[N:30]=[CH:29][NH:28][CH:27]=2)=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178501435HCID 178501435, compound

Product 1

HCID 178445997HCID 178445997, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5.1 g of p-acetoxyhippuryl-L-histidyl-L-leucine methyl ester is dissolved in 20 ml of methanol, and to this solution is added 20 ml of a 1 N.aqueous solution of NaOH at a temperature of 4° C., and after stirring for one hour, the pH of the solution is lowered to 5 by adding HCl, and water and methanol are distilled off. The residue is dissolved in methanol and filtered, and to this solution is added ethyl ether. The crystals deposited after standing at -20° C. are filtered to obtain p-hydroxyhippuryl-L-histidyl-L-leucine.

Workup

  1. additionto this solution is added 20 ml of a 1 N
  2. distillationare distilled off
  3. dissolutionThe residue is dissolved in methanol
  4. filtrationfiltered
  5. additionto this solution is added ethyl ether
  6. customafter standing at -20° C.
  7. filtrationare filtered

Sources & evidence

ORD record
ord-3e788174a1ac4297b7ce08c24e6eaaa5
Source dataset
uspto-grants-1981_09
Patent number
US04292404

Reaction notes

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