tert-Butyldimethylsilyl chloride → N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine

HRID 1035553노트

반응식

HRID 1035553 반응식
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C@@H:12]([CH3:15])[CH2:13][OH:14])[C:5]([CH3:16])=[C:4]([CH3:17])[N:3]=1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[Si:18]([O:14][CH2:13][C@@H:12]([NH:11][C:6]1[C:5]([CH3:16])=[C:4]([CH3:17])[N:3]=[C:2]([Cl:1])[C:7]=1[N+:8]([O-:10])=[O:9])[CH3:15])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

참가 물질

5

반응물 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 86624127(2S)-2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]propan-1-ol

생성물 1

HCID 86624128N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine수율 92.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

반응 조건

온도
50 °C

실험 절차

(2S)-2-[(2-Chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]propan-1-ol (3.62 g, 13.9 mmol) was dissolved in 30 mL of dry pyridine under an atmosphere of N2. tert-Butyldimethylsilyl chloride (2.52 g, 16.7 mmol) and DMAP (0.17 g, 1.39 mmol) were added sequentially, and the reaction was heated to 50° C. and stirred overnight. The reaction mixture was then concentrated under reduced pressure. The resulting residue was partitioned between 50 mL of ethyl acetate and 50 mL of H2O. The layers were separated and the organic portion was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting material was passed through a plug of SiO2, eluting with a mixture of CH2Cl2, ethyl acetate and hexanes, to afford N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine (4.79 g) as an orange oil.

후처리

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe resulting residue was partitioned between 50 mL of ethyl acetate and 50 mL of H2O
  3. customThe layers were separated
  4. washthe organic portion was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washeluting with a mixture of CH2Cl2, ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-0a66a1fc77bb4613b3a87e2b12ba1a79
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546383B2

반응 노트

불러오는 중…