Carbon Disulfide → (4S)-3,4-diisobutyl-1,3-thiazolidin-2-thione

HRID 276275ノート

反応式

HRID 276275 の反応式
Cl.[CH3:2][CH:3]([CH3:13])[CH2:4][C@H:5]([NH:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:6]O.[C:14](=[S:16])=[S:15].C([O-])([O-])=O.[Cs+].[Cs+]>CC(=O)CC>[CH2:9]([N:8]1[C@@H:5]([CH2:4][CH:3]([CH3:13])[CH3:2])[CH2:6][S:16][C:14]1=[S:15])[CH:10]([CH3:12])[CH3:11]

参加物

5

反応物 3

HCID 6348Carbon DisulfideHCID 10796Cesium carbonateHCID 86590169HCID 86590169、化合物

生成物 1

HCID 22951238(4S)-3,4-diisobutyl-1,3-thiazolidin-2-thione収率 52%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

To a mixture of (2S)4-methyl-2-(isobutylamino)pentan-1-ol HCl salt (Method B4c; 0.21 g, 1.0 mmol) and CS2 (0.30 mL, 5.0 mmol, 5.0 equiv.) in 2-butanone (20 mL) was added Cs2CO3 (0.72 g, 2.20 mmol, 2.2 equiv.) and the resulting mixture was heated at the reflux temp. overnight. The resulting orange solution was concentrated under reduced pressure and the residue was triturated with EtOAc (25 mL). The remaining solids were washed with EtOAc (25 mL), and the combined EtOAc phases were concentrated under reduced pressure. The residue was absorbed onto SiO2 and purified by MPLC (Biotage 40 S silica gel column; 5% EtOAc/hex) to give (4S)-3,4diisobutyl 1,3-thiazolidin-2-thione as a yellow oil (0.11 g, 52%).

後処理

  1. temperaturethe resulting mixture was heated at the reflux temp
  2. customovernight
  3. concentrationThe resulting orange solution was concentrated under reduced pressure
  4. customthe residue was triturated with EtOAc (25 mL)
  5. washThe remaining solids were washed with EtOAc (25 mL)
  6. concentrationthe combined EtOAc phases were concentrated under reduced pressure
  7. customThe residue was absorbed onto SiO2
  8. custompurified by MPLC (Biotage 40 S silica gel column; 5% EtOAc/hex)

出典と根拠

ORDレコード
ord-ad41081e9c124d19afa1a109119e4d25
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

反応ノート

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