Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 15908470, compound

HRID 480024Notes

Reaction equation

HRID 480024 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:15])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].[S:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.Cl[C:39]([N:41]=[C:42]=[O:43])=[O:40]>C1(C)C=CC=CC=1>[O:40]=[C:39]1[N:1]([CH2:2][CH2:3][CH2:4][N:5]([CH3:15])[S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:8])=[O:7])[C:19]2[CH2:18][CH2:17][S:16][CH2:21][C:20]=2[C:42](=[O:43])[NH:41]1

Participants

6

Reactant 4

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 66173Tetrahydrothiopyran-4-oneHCID 119708Isocyanatocarbonyl chlorideHCID 28387092HCID 28387092, compound

Product 1

HCID 15908470HCID 15908470, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.98 g (4.3 mmol) of N-(3-aminopropyl)-N-methylphenylsulphonamide [preparation according to P. Daetwyler et al., Helv. Chim. Acta, 61, 2646 (1978)], 0.55 g (4.73 mmol) of tetrahydrothiopyran-4-one and a catalytic amount of camphorsulphonic acid in 50 ml of toluene is heated at reflux for 3 hours using a Dean-Stark separator. After cooling to room temperature, the Dean-Stark separator is removed, 0.54 g (5.16 mmol) of chlorocarbonyl isocyanate are added and the mixture is refluxed for another hour. The solvent is removed using a rotary evaporator and the resulting residue is purified by preparative HPLC (RP-C18, acetonitrile/water gradient). This gives 717 mg (42% yield) of an amorphous solid.

Workup

  1. temperatureat reflux for 3 hours
  2. customthe Dean-Stark separator is removed
  3. temperaturethe mixture is refluxed for another hour
  4. customThe solvent is removed
  5. customa rotary evaporator
  6. customthe resulting residue is purified by preparative HPLC (RP-C18, acetonitrile/water gradient)

Sources & evidence

ORD record
ord-59507797d8c1461cb5e256b75799f333
Source dataset
uspto-grants-2003_11
Patent number
US06649618B2

Reaction notes

Loading…