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

HRID 480024ノート

反応式

HRID 480024 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 15908470HCID 15908470、化合物収率 42.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-59507797d8c1461cb5e256b75799f333
出典データセット
uspto-grants-2003_11
特許番号
US06649618B2

反応ノート

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