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

HRID 480024노트

반응식

HRID 480024 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 15908470HCID 15908470, 화합물수율 42.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-59507797d8c1461cb5e256b75799f333
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649618B2

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