Trifluoroacetic acid → HCID 69607355, 화합물

HRID 1244158노트

반응식

HRID 1244158 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][S:8][C:7]=1[NH:19]C(OC(C)(C)C)=O)=[O:5])[CH3:2].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][S:8][C:7]=1[NH2:19])=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acid2회HCID 516892Sodium BicarbonateHCID 69607320HCID 69607320, 화합물

생성물 1

HCID 69607355HCID 69607355, 화합물수율 56%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-t-Butoxycarbonylamino-4-styryl-thiophene-3-carboxylic acid ethyl ester (0.335 g, 0.848 mmol) was dissolved in anhydrous CH2Cl2 (8 mL). This was treated with trifluoroacetic acid (0.346 mL, 4.49 mmol) and stirred at room temperature for 6 hr. More trifluoroacetic acid (0.346 mL, 4.49 mmol) was added and stirring at room temperature was continued for 30 min. The reaction was neutralized with sat. NaHCO3 (25 mL) and then extracted with CH2Cl2 (2×25 mL). The combined organic layers were washed with H2O (1×25 mL) and brine (1×25 mL). The organic layer was then dried (Na2SO4), filtered and the solvent removed in vacuo. The crude product was purified by flash chromatography (SiO2, 15 EtOAc/85 hexanes) to afford the title compound (0.1298 g, 56%) as an inseparable mixture. MS m/e (CI) 274.0 (M+H)+; 1H NMR (300 MHz, CDCl3): δ ppm 0.85 (d, 1H), 1.32 (m, 4H), 4.26 (m, 1H), 6.75 (s, 1H), 7.18 (m, 4H), 7.35 (d, 1H), 7.52 (d, 1H), 7.66 (d, 1H), 7.78 (s, 1H).

후처리

  1. stirringstirring at room temperature
  2. waitwas continued for 30 min
  3. extractionextracted with CH2Cl2 (2×25 mL)
  4. washThe combined organic layers were washed with H2O (1×25 mL) and brine (1×25 mL)
  5. dry with materialThe organic layer was then dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe crude product was purified by flash chromatography (SiO2, 15 EtOAc/85 hexanes)

출처 및 근거

ORD 기록
ord-4cf4efd5ad8f42a6836fc444bced04df
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119205B2

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