N-(2-hydroxyethyl)nicotinamide → HCID 16113761, 화합물

HRID 602239

반응식

HRID 602239 반응식
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[N:8][CH:7]=1.[C:13]1([CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl.N1C=CC=CC=1>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:5]([NH:4][CH2:3][CH2:2][O:1][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH:7]=1

참가 물질

5

반응물 2

HCID 72663N-(2-hydroxyethyl)nicotinamideHCID 117898654-Phenylbutanoyl Chloride

생성물 1

HCID 16113761HCID 16113761, 화합물수율 100%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

반응 조건

온도
2 °C

실험 절차

N-(2-Hydroxy-ethyl)-nicotinamide (3.3 g, 20.0 mmol, 1.0 eq.) was dissolved in DCM (100 mL) and pyridine (20 mL). The light yellow solution was cooled to 2° C. A solution of 4-phenylbutanoylchloride (3.65 g of 20 mmol, 1.0 eq.) in DCM (25 mL) was slowly added. The reaction mixture was stirred for 1 h at 0° C. The reaction mixture was evaporated under reduced pressure and the residue was dissolved in water (100 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous phase was extracted with ethyl acetate (75 mL). The combined organic layers were washed with a saturated aqueous solution of NaHCO3 (50 mL) and of brine (50 mL). The organic layer was dried over Na2SO4, filtrated and evaporated under reduced pressure. The yellow, oily residue was dried at high vacuum at room temperature to give 6.2 g (100%) of the product as yellow oil. The crude product was purified by flash chromatography over silica gel with ethyl acetate to yield the pure 4-phenyl-butyric acid 2-[(pyridine-3-carbonyl)amino]-ethyl ester 5.6 g (89%) as a light yellow oil. 1H NMR (CDCl3) δ=1.87-1.95 (m, 2H), 2.29-2.34 (m, 2H), 2.58-2.63 (m, 2H), 3.67-3.72 (m, 2H), 4.25-4.29 (m, 2H), 7.11-7.41 (m, 7H), 8.08-8.12 (m, 1H), 8.65-8.67 (q, 1H), 8.99-9.00 (d, 1H). 13C NMR (CDCl3) δ=26.3, 33.4, 35.0, 39.6, 62.9, 123.5, 126.0, 128.4, 128.4, 130.0, 135.2, 141.1, 148.1, 152.1, 165.8, 173.9. MS (ESI) m/z=313.2 (100) [M+H+]. DC (silica gel/ethyl acetate): RF=0.32.

후처리

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (75 mL)
  5. washThe combined organic layers were washed with a saturated aqueous solution of NaHCO3 (50 mL) and of brine (50 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltrated
  8. customevaporated under reduced pressure
  9. customThe yellow, oily residue was dried at high vacuum at room temperature

출처 및 근거

ORD 기록
ord-9b672d4fb9ba45ba9e703b1148095f09
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906496B2

연결된 노트

불러오는 중…