Sodium borohydride → N-[1-(1,3-benzothiazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide

HRID 2108840노트

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HRID 2108840 반응식
[S:1]1[C:5]2[CH:6]=[C:7]([C:10](=O)[CH3:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH3:13][C:14]([S@:17]([NH-:19])=[O:18])([CH3:16])[CH3:15].[BH4-].[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.C1COCC1>[S:1]1[C:5]2[CH:6]=[C:7]([CH:10]([NH:19][S:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])[CH3:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

참가 물질

6

반응물 3

HCID 4311764Sodium borohydrideHCID 108211871-(1,3-Benzothiazol-6-yl)ethan-1-oneHCID 86609349(R)-t-butylsulfinylamide

생성물 1

HCID 68843346N-[1-(1,3-benzothiazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide

시약·촉매·용매 2

HCID 76524Titanium tetraethoxide촉매HCID 8028Tetrahydrofuran용매

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온도
85 °C

실험 절차

To a THF (6 ml) solution of 1-(1,3-benzothiazol-6-yl)ethanone (European Journal of Organic Chemistry (1998), (9), 2047-2050., 250 mg, 1.41 mmol) and (R)-(+)-2-methyl-2-propane sulfinylamide (188 mg, 1.55 mmol), titanium(IV) ethoxide (2 ml) was added and the mixture was stirred for 40 minutes at 85° C. under microwave condition. The mixture was then cooled to 0° C. and sodium borohydride (188 mg, 5.0 mmol) was added to the reaction mixture. After stirring for 2 hours at the temperature, the reaction was partitioned with water and EtOH followed by stirring for 1 hour at room temperature. Then, filtration, evaporation gave N-[1-(1,3-benzothiazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide (MS (ESI) m/z 281 (M−H)−, 283 (M+H)+) which was then added hydrochloric acid-MeOH (2.0 M, 7.0 ml) and 1,4-dioxane (7.0 ml). The mixture was then stirred for 1.5 hours at room temperature and the same reaction procedure as Example 14 was performed to give the title compound. MS (ESI) m/z 180 (M−H)+

후처리

  1. temperatureThe mixture was then cooled to 0° C.
  2. stirringAfter stirring for 2 hours at the temperature
  3. customthe reaction was partitioned with water and EtOH
  4. stirringby stirring for 1 hour at room temperature
  5. filtrationThen, filtration, evaporation

출처 및 근거

ORD 기록
ord-bdf259c3edc845d2bce40ff1f8583d7a
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514457B2

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