Acetone → HCID 86741593, compound

HRID 652784Notes

Reaction equation

HRID 652784 reaction equation
[CH3:1][O:2][CH:3]1[C:11](=[S:12](=[O:14])=[O:13])[C:10]([O:15][CH3:16])=[C:9]([CH3:17])[CH:8]=[C:4]1[C:5]([OH:7])=O.CC(C)=O.ClC(OCC)=O.[CH:28]1([N:36]2[CH2:40][CH2:39][CH2:38][CH:37]2[CH2:41][NH2:42])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C(N(CC)CC)C.O>[CH:28]1([N:36]2[CH2:40][CH2:39][CH2:38][CH:37]2[CH2:41][NH:42][C:5](=[O:7])[C:4]2[CH:3]([O:2][CH3:1])[C:11](=[S:12](=[O:14])=[O:13])[C:10]([O:15][CH3:16])=[C:9]([CH3:17])[CH:8]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 10928Ethyl chloroformateHCID 20196835HCID 20196835, compoundHCID 86741591HCID 86741591, compound

Product 1

HCID 86741593HCID 86741593, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

13 g of 2,4-dimethoxy-5-methyl sulphonyl benzoic acid, 150 ml of acetone, 28 ml of water and 7 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 suspension is cooled to from 0° to +5° C., then 5.4 g of ethyl chloroformate is added drop by drop. The mixture is agitated for 45 minutes at room temperature and cooled to about 0° C., then 13.8 g of 1-cyclooctyl-2-aminomethyl-pyrrolidine is added drop by drop. There is complete solubilisation. The reaction medium is agitated at room temperature then left to stand. The solvents are evaporated under vacuum and the residue is dissolved in 100 ml of water and 20 ml of hydrochloric acid (density 1.18). The organic phase is extracted 3 times with 50 ml of methylene chloride, dried over magnesium sulphate, filtered and evaporated to dryness under vacuum. The residue is dissolved in 100 ml of water. The solution is filtered in the presence of carbon black and the filtrate made alkaline with 10 ml of ammonia. A gum is precipitated. This is extracted 3 times with 50 ml of methylene chloride, and the organic solution is washed twice with 50 ml of water and dried over magnesium sulphate. It is filtered, then the solvent is evaporated under vacuum and the residue re-crystallised in 200 ml of isopropanol. The crystals are filtered off, washed twice with a little iced isopropanol and dried in an oven at 50° C.

Workup

  1. customfitted with an agitator
  2. temperatureThe suspension is cooled to from 0° to +5° C.
  3. temperaturecooled to about 0° C.
  4. stirringThe reaction medium is agitated at room temperature
  5. waitthen left
  6. customThe solvents are evaporated under vacuum
  7. dissolutionthe residue is dissolved in 100 ml of water
  8. extractionThe organic phase is extracted 3 times with 50 ml of methylene chloride
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated to dryness under vacuum
  12. dissolutionThe residue is dissolved in 100 ml of water
  13. filtrationThe solution is filtered in the presence of carbon black
  14. customA gum is precipitated
  15. extractionThis is extracted 3 times with 50 ml of methylene chloride
  16. washthe organic solution is washed twice with 50 ml of water
  17. dry with materialdried over magnesium sulphate
  18. filtrationIt is filtered
  19. customthe solvent is evaporated under vacuum
  20. customthe residue re-crystallised in 200 ml of isopropanol
  21. filtrationThe crystals are filtered off
  22. washwashed twice with a little iced isopropanol
  23. customdried in an oven at 50° C.

Sources & evidence

ORD record
ord-f522851b2ea84ab59214c07eb8877fc1
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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