N-(2-hydroxyethyl)nicotinamide → HCID 16113761、化合物

HRID 602239

反応式

HRID 602239 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 16113761HCID 16113761、化合物収率 100%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
2 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9b672d4fb9ba45ba9e703b1148095f09
出典データセット
uspto-grants-2011_03
特許番号
US07906496B2

関連ノート

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