2-Chloro-4-fluorobenzonitrile → HCID 59516164, 화합물

HRID 1160389노트

반응식

HRID 1160389 반응식
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:11][C@@H:12]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([OH:15])=[O:14].C([O-])(O)=O.[Na+]>CS(C)=O.O>[Cl:1][C:2]1[CH:9]=[C:8]([NH:11][C@@H:12]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([OH:15])=[O:14])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

6

반응물 3

HCID 1090002-Chloro-4-fluorobenzonitrileHCID 516892Sodium BicarbonateHCID 70105704-tert-Butyl hydrogen L-aspartate

생성물 1

HCID 59516164HCID 59516164, 화합물수율 80.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회

실험 절차

2-Chloro-4-fluorobenzonitrile (2.13 g, 13.8 mmol), (2S)-2-amino-4-[(1,1-dimethylethyl)oxy]-4-oxobutanoic acid (2.6 g, 13.8 mmol) and NaHCO3 (3.5 g, 41.4 mmol) in DMSO (70 mL) and H2O (10 mL) were stirred at 95° C. for 15 h. After cooling, the reaction mixture was diluted with H2O (100 mL) and washed with Et2O (100 mL). The H2O layer was acidified to Congo Red midpoint and extracted with Et2O (2×). The combined organic extracts were washed with H2O, dried over Na2SO4, filtered, and concentrated to give the titled product (3.59 g, 80%) as a foam. 1H-NMR (CDCl3) δ: 1.45 (9H, s), 2.89 (2H, m), 3.54 (1H, m), 4.42 (1H, m), 6.55 (1H, d, J=8.8 Hz), 6.70 (1H, s), 7.43 (1H, d, J=8.4 Hz). LC-MS (ES) m/e 325.4 (M+H)+.

후처리

  1. temperatureAfter cooling
  2. washwashed with Et2O (100 mL)
  3. extractionextracted with Et2O (2×)
  4. washThe combined organic extracts were washed with H2O
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c27368e9aa0d450b899c47fa43380268
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816395B2

반응 노트

불러오는 중…