Hydrogen Sulfide → HCID 86753666, compound

HRID 361743Notes

Reaction equation

HRID 361743 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:33])[C:18]([CH3:32])([CH3:31])[CH2:19][NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S.[N:36]1C=CC=CC=1>>[CH2:1]([O:8][C:9](=[O:34])[CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:33])[C:18]([CH3:31])([CH3:32])[CH2:19][NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([C:28](=[NH:36])[NH2:29])=[CH:24][CH:23]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 86753667HCID 86753667, compound

Product 1

HCID 86753666HCID 86753666, compoundYield 40%

Procedure

N-(N-4-Cyanobenzoyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid benzyl ester (0.6 g) was dissolved in pyridine (15 ml) and hydrogen sulfide gas was introduced for 1 hour. The reaction container was sealed and the reaction mixture was stirred at a room temperature for 12 hours. The solvent was distilled off and methyl iodide (2 g) was added, followed by refluxing in acetone for 3 hours. After the solvent and excess methyl iodide were distilled off from the reaction solution, ammonium acetate (0.2 g) was added and the mixture was refluxed in methanol for 6 hours. After the solvent was distilled off, the residue was dissolved in a small amount of methylene chloride and reprecipitated from hexane to yield N-(N-4-amidinobenzoyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid benzyl ester (0.25 g, 40.0%).

Workup

  1. customThe reaction container was sealed
  2. distillationThe solvent was distilled off
  3. additionmethyl iodide (2 g) was added
  4. temperatureby refluxing in acetone for 3 hours
  5. distillationAfter the solvent and excess methyl iodide were distilled off from the reaction solution, ammonium acetate (0.2 g)
  6. additionwas added
  7. temperaturethe mixture was refluxed in methanol for 6 hours
  8. distillationAfter the solvent was distilled off
  9. dissolutionthe residue was dissolved in a small amount of methylene chloride
  10. customreprecipitated from hexane

Sources & evidence

ORD record
ord-e5547cfa663d405aa4052207313edae7
Source dataset
uspto-grants-1999_02
Patent number
US05866592

Reaction notes

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