Pyridine → 4,4,4-Trifluoro-2-(4-fluoro-3-methyl-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl ester

HRID 1987582노트

반응식

HRID 1987582 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:12].[CH2:13]([O:15][C:16](=[O:28])[CH:17]([NH2:27])[CH:18]([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])[CH3:14].N1C=CC=CC=1>ClC(Cl)C>[CH2:13]([O:15][C:16](=[O:28])[CH:17]([NH:27][S:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH3:12])[CH:4]=1)(=[O:10])=[O:9])[CH:18]([C:19]([F:22])([F:20])[F:21])[C:23]([F:25])([F:26])[F:24])[CH3:14]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 27827584-Fluoro-3-methylbenzene-1-sulfonyl chlorideHCID 529919404,4,4,4',4',4'-Hexafluorovaline, ethyl ester

생성물 1

HCID 866160074,4,4-Trifluoro-2-(4-fluoro-3-methyl-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl ester수율 64.7%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a vial containing a solution of 4-fluoro-3-methylbenzenesulfonyl chloride (50 mg, 0.24 mmol) and 2-amino-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester (61 mg, 0.24 mmol) in anhydrous dichloroethane (1 mL) was added pyridine (58 μL, 0.719 mmol). The vial was capped and shaken for 18 h. The solvent was removed in vacuo and the residue transferred to a separatory funnel with EtOAc (100 mL) and washed with distilled water (100 mL×2). The organic layer was removed and the combined aqueous washings were extracted with EtOAc (100 mL×2). The organic extracts were combined, washed with brine (100 mL), dried (MgSO4), filtered, and evaporated to give a white solid (66 mg). This material was purified by Gilson RP-HPLC (column YMC Combiprep 50×20 mm, gradient 10-100% CH3CN: H2O) to afford a white solid (29 mg, 28%). Mass Spectrum (−ESI): 424 [M−H]−.

후처리

  1. customThe vial was capped
  2. customThe solvent was removed in vacuo
  3. customthe residue transferred to a separatory funnel with EtOAc (100 mL)
  4. washwashed with distilled water (100 mL×2)
  5. customThe organic layer was removed
  6. extractionthe combined aqueous washings were extracted with EtOAc (100 mL×2)
  7. washwashed with brine (100 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

출처 및 근거

ORD 기록
ord-b5e6f40a4747459e82954a9e0640e8f9
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550629B2

반응 노트

불러오는 중…