Hydrochloric Acid → HCID 54368508, compound

HRID 273829Notes

Reaction equation

HRID 273829 reaction equation
C([O:3][C:4](=[O:30])[C@H:5]([CH2:20][C:21]1[N:25]=[C:24]([S:26][CH2:27][CH2:28][CH3:29])[NH:23][CH:22]=1)[N:6](CC1C=CC=CC=1Cl)[C:7](=[O:11])[CH2:8][CH2:9][CH3:10])C.[CH2:31](O)[CH3:32].[OH-].[K+].[ClH:36]>O>[Cl:36][C:22]1[CH:21]=[CH:20][CH:5]=[CH:4][C:31]=1[CH2:32][N:25]1[C:21]([CH2:20][C@@H:5]([C:4]([OH:3])=[O:30])[NH:6][C:7](=[O:11])[CH2:8][CH2:9][CH3:10])=[CH:22][N:23]=[C:24]1[S:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 178460789HCID 178460789, compound

Product 1

HCID 54368508HCID 54368508, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of 3-[(2-chlorophenyl)methyl-2-propylthio-N-butyrylhistidine ethyl ester (0.37 g, 0.819 mmole), ethanol (4 mL), water (4 mL) and potassium hydroxide pellets (0.098 g, 1.75 mmole) was stirred at 25° C. for 1 hour. The reaction was then diluted with water and the pH was adjusted to 4 with 1N aqueous hydrochloric acid solution. The product was extracted into methylene chloride, washed with water, dried and concentrated to an orange solid. Two crystallizations from chloroform provided 0.22 g of 3-[(2-chlorophenyl)methyl]-2-propylthio-N-butyrylhistidine; m.p. 178°-181° C.

Workup

  1. extractionThe product was extracted into methylene chloride
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated to an orange solid
  5. customTwo crystallizations from chloroform

Sources & evidence

ORD record
ord-90c9f51de3aa44fabc216c3f56fb62ae
Source dataset
uspto-grants-1995_02
Patent number
US05387601

Reaction notes

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