Potassium Carbonate → Dicyclohexylamine

HRID 544495Notes

Reaction equation

HRID 544495 reaction equation
Cl[C:2]1[CH:16]=[CH:15][C:5](C(SCC(C)C(Cl)=O)=O)=[CH:4][C:3]=1S(=O)(=O)N.[NH:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23](O)=O.[C:29](=O)([O-])[O-].[K+].[K+]>CCOCC>[CH:28]1([NH:21][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:15][CH2:16]2)[CH2:27][CH2:26][CH2:22][CH2:23][CH2:29]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 12767893HCID 12767893, compound

Product 1

HCID 7582Dicyclohexylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.2 g of 3-(4-chloro-3-sulfamoylbenzoylthio)-2-methylpropionyl chloride in 15 ml ofether is added dropwise to a mixture of 1.6 g of L-proline, aqueous 1 N potassium carbonate solution and 20 ml of ether under ice-cooling and stirring, and the resulting mixture is stirred at room temperature for 2 hours. The aqueous layer is then collected and acidic with dilute hydrochloric acid, and the separated oil is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is dissolved in acetonitrile and 2 g of dicylohexylamine is added. The oil thus obtained is washed several times with acetonitrile by decantation. The resulting crystals are recrystallized from isopropanol to give dicylohexylamine saltof 1-[3-(4-chloro-3-sulfamoylbenzoylthio)-2(S)-methylpropionyl]-L-proline as white crystalline powder, melting at 143°-146° C.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture is stirred at room temperature for 2 hours
  3. customThe aqueous layer is then collected and acidic with dilute hydrochloric acid
  4. extractionthe separated oil is extracted with ethyl acetate
  5. washThe extract is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue is dissolved in acetonitrile
  9. addition2 g of dicylohexylamine is added
  10. customThe oil thus obtained
  11. washis washed several times with acetonitrile by decantation
  12. customThe resulting crystals are recrystallized from isopropanol

Sources & evidence

ORD record
ord-5601016b654b43e8a837b5786df1cd88
Source dataset
uspto-grants-1984_05
Patent number
US04450275

Reaction notes

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