Methanesulfonyl chloride → HCID 13561105, compound

HRID 466376Notes

Reaction equation

HRID 466376 reaction equation
[CH2:1]([N:3]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)[CH3:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH2:1]([N:3]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([NH:14][S:23]([CH3:22])(=[O:25])=[O:24])[CH:11]=[CH:12][CH:13]=1)[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19873398HCID 19873398, compound

Product 1

HCID 13561105HCID 13561105, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The amine from Step IV (1.7 g, 0.00585 mol) is mixed with 4.6 ml of pyridine under nitrogen, the mixture cooled in an ice bath and treated dropwise, over 5 min, with 0.5 ml (0.74 g, 0.0064 mol) of methanesulfonyl chloride. The mixture is stirred in the cold for 1 hr and at room temperature overnight. The solvent is removed in vacuo as an azetrope with toluene. The residue is taken up in CH2Cl2 (75 ml), washed with 25 ml of 8% NaHCO3 and the aqueous wash extracted with CH2Cl2 (2×75 ml). The organic pool is washed with brine, dried (Na2SO4) and concentrated to give a dark oil. This material is chromatographed over 500 ml of silica gel (eluted with 0.4% NH4OH-8% MeOH--CH2Cl2); 45 ml fractions are collected. The resulting material is further treated with cold, dilute NaOH to pH 12 and extracted with EtOAc (1×40 ml). The organic extract is washed with cold, dilute NaOH (2×5 ml) and the pooled aqueous wash extracted with EtOAc (2×25 ml) (each extract is washed with 5 ml of H2O). The pooled EtOAc extract is dried (Na2SO4) and concentrated in vacuo to give the title compound. The title compound is chromatographed over 50 ml of silica gel (eluted with 0.25% NH4OH-10% MeOH--CH2Cl2) and 20 ml fractions collected. Theory for C20H37N2O2S 369.2576; measured, 369.2576 by high resolution FAB MS. ##STR1##

Workup

  1. temperaturethe mixture cooled in an ice bath
  2. customat room temperature
  3. customovernight
  4. customThe solvent is removed in vacuo as an azetrope with toluene
  5. washwashed with 25 ml of 8% NaHCO3
  6. washthe aqueous wash
  7. extractionextracted with CH2Cl2 (2×75 ml)
  8. washThe organic pool is washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customto give a dark oil
  12. customThis material is chromatographed over 500 ml of silica gel (eluted with 0.4% NH4OH-8% MeOH--CH2Cl2)
  13. custom45 ml fractions are collected
  14. additionThe resulting material is further treated with cold, dilute NaOH to pH 12
  15. extractionextracted with EtOAc (1×40 ml)
  16. extractionThe organic extract
  17. washis washed with cold, dilute NaOH (2×5 ml)
  18. washthe pooled aqueous wash
  19. extractionextracted with EtOAc (2×25 ml) (each extract
  20. washis washed with 5 ml of H2O)
  21. extractionThe pooled EtOAc extract
  22. dry with materialis dried (Na2SO4)
  23. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f21f4f076e3c405ca405be92ad356bde
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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