Acetone → HCID 86741589, compound

HRID 652776Notes

Reaction equation

HRID 652776 reaction equation
[CH3:1][O:2][CH:3]1[C:11](=[S:12](=[O:14])=[O:13])[C:10]([NH2:15])=[C:9]([CH2:16][CH3:17])[CH:8]=[C:4]1[C:5]([OH:7])=O.[CH3:18]C(C)=O.ClC(OCC)=O.[CH:28]1([N:35]2[CH2:39][CH2:38][CH2:37][C:36]2(C)[CH2:40][NH2:41])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C(N(CC)CC)C.O>[CH:28]1([N:35]2[CH2:39][CH2:38][CH2:37][CH:36]2[CH:40]([CH3:18])[NH:41][C:5](=[O:7])[C:4]2[CH:3]([O:2][CH3:1])[C:11](=[S:12](=[O:14])=[O:13])[C:10]([NH2:15])=[C:9]([CH2:16][CH3:17])[CH:8]=2)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 10928Ethyl chloroformateHCID 54502136HCID 54502136, compoundHCID 86681511HCID 86681511, compound

Product 1

HCID 86741589HCID 86741589, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

4.9 g of 2-methoxy-4-amino-5-ethyl sulphonyl benzoic acid, 57 ml of acetone, 10 ml of water and 2.6 ml of triethylamine (density 0.726) are placed in a 250 ml flask fitted with an agitator, a thermometer, a condenser and a dropping funnel. The solution is cooled to between 0° and +5° C. and 2.1 g of ethyl chloroformate is added drop by drop. The reaction medium is agitated for 45 minutes at room temperature then cooled to 0° C. and 5.3 g of 1-cycloheptyl methyl-2-amino methyl pyrrolidine is poured in drop by drop. The medium is agitated for 4 hours then left to stand overnight. The solvents are evaporated to dryness and the residue is dissolved in 60 ml of water and 15 ml of hydrochloric acid (density 1.18). Extraction is carried out 3 times with 50 ml of methylene chloride, the organic phase is dried over magnesium sulphate and filtered, and the solvent is evaporated under vacuum. The residue is dissolved in 100 ml of water. The solution is filtered in the presence of carbon black and the filtrate is made alkaline with about 7 ml of ammonia (density 0.91). A gum is precipitated. It is extracted 3 times with 50 ml of methylene chloride. The organic phase is washed twice with 50 ml of water, dried over magnesium sulphate and filtered. The solvent is evaporated under vacuum and the residue is re-crystallised in 100 ml of isopropanol.

Workup

  1. customfitted with an agitator
  2. temperatureThe solution is cooled to between 0° and +5° C.
  3. temperaturethen cooled to 0° C.
  4. stirringThe medium is agitated for 4 hours
  5. waitthen left
  6. waitto stand overnight
  7. customThe solvents are evaporated to dryness
  8. dissolutionthe residue is dissolved in 60 ml of water
  9. extractionExtraction
  10. dry with materialthe organic phase is dried over magnesium sulphate
  11. filtrationfiltered
  12. customthe solvent is evaporated under vacuum
  13. dissolutionThe residue is dissolved in 100 ml of water
  14. filtrationThe solution is filtered in the presence of carbon black
  15. customA gum is precipitated
  16. extractionIt is extracted 3 times with 50 ml of methylene chloride
  17. washThe organic phase is washed twice with 50 ml of water
  18. dry with materialdried over magnesium sulphate
  19. filtrationfiltered
  20. customThe solvent is evaporated under vacuum
  21. customthe residue is re-crystallised in 100 ml of isopropanol

Sources & evidence

ORD record
ord-2df1bb6728664843bb0ad2982a648a47
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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