tert-Butylsulfinamide, (R)-(+)- → (NZ)-2-methyl-N-[1-(2-methylsulfonyl-1,3-thiazol-5-yl)propylidene]propane-2-sulfinamide

HRID 1423041

반응식

HRID 1423041 반응식
[CH3:1][S:2]([C:5]1[S:6][C:7]([C:10](=O)[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:4])=[O:3].[CH3:14][C:15]([S@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C1COCC1.C(OCC)C.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][S:2]([C:5]1[S:6][C:7](/[C:10](=[N:20]\[S:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])/[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:4])=[O:3]

참가 물질

7

반응물 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 592783971-(2-Methanesulfonyl-thiazol-5-yl)-propan-1-one

생성물 1

HCID 87126692(NZ)-2-methyl-N-[1-(2-methylsulfonyl-1,3-thiazol-5-yl)propylidene]propane-2-sulfinamide

시약·촉매·용매 4

HCID 11026Titanium isopropoxide촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 1-(2-methanesulfonyl-thiazol-5-yl)-propan-1-one (110 mg, 0.50 mmol), (R)-2-methyl-2-propanesulfinamide (70 mg, 0.6 mmol) and titanium (IV) isopropoxide (0.29 mL, 1.0 mmol) in THF (10 mL) is warmed at reflux. After 18 hours, the mixture is cooled to room temperature and diluted with diethyl ether (100 mL) and water (6 mL). After 10 minutes with stirring, the solution is dried over sodium sulfate, filtered and concentrated. The crude product is purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes to afford 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide.

후처리

  1. temperatureis warmed
  2. temperatureat reflux
  3. dry with materialthe solution is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel chromatography
  7. washeluting with a gradient of 0-100% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-cd07506f52b145dbb3b0cede6d322b09
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927550B2

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