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

HRID 276275노트

반응식

HRID 276275 반응식
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]

참가 물질

5

반응물 3

HCID 6348Carbon DisulfideHCID 10796Cesium carbonateHCID 86590169HCID 86590169, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ad41081e9c124d19afa1a109119e4d25
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353006B1

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