Bromotrimethylsilane → [2-Phenyl-1-(thiophene-2-sulfonylamino)-ethyl]phosphonic acid

HRID 896987

반응식

HRID 896987 반응식
C([O:3][P:4]([CH:9]([NH:17][S:18]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)(=[O:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>ClCCl>[C:11]1([CH2:10][CH:9]([P:4](=[O:3])([OH:5])[OH:8])[NH:17][S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

4

반응물 2

HCID 76113BromotrimethylsilaneHCID 228909322-Phenyl-1-(thiophene-2-sulfonylamino)-ethyl-phosphonic Acid Diethyl Ester

생성물 1

HCID 22179290[2-Phenyl-1-(thiophene-2-sulfonylamino)-ethyl]phosphonic acid수율 81.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of diethyl phosphonate (xii) (745 mg; 1.8 mmol) in dichloromethane (8 mL) at 0° C. was slowly added bromotrimethylsilane (2 mL; 15.2 mmol). The reaction was gradually warmed to room temperature and the following day the solution was evaporated. The residue was redissolved in dichloromethane (10 mL), evaporated and the process repeated once more. Methanol (10 mL) was added to the residue and the solution stirred at room temperature for 30 minutes, then the solution was filtered and concentrated. The oily residue was triturated with 1:1 ether-hexanes and the orange solid collected by filtration. Finally, the orange solid was boiled in dichloromethane (5 mL), cooled and filtered to yield pure phosphonic acid (xiii) (512 mg, 80%) as a colorless solid: 1H NMR (400 MHz, CD3OD) δH 2.71 (dt, J=14, 10 Hz, 1H, CHPh), 3.13 (ddd, J=4, 8, 14 Hz, 1H, CHPh), 3.89 (ddd, J=4, 10, 14 Hz, NCHP), 6.86 (dd, J=3.5, 5 Hz, 1H, Ar—H), 7.07-7.15 (m, 6H, Ar—H), 7.53 (dd, J=1.5, 5 Hz, 1H, Ar—H).

후처리

  1. customat 0° C.
  2. customthe following day the solution was evaporated
  3. dissolutionThe residue was redissolved in dichloromethane (10 mL)
  4. customevaporated
  5. additionMethanol (10 mL) was added to the residue
  6. filtrationthe solution was filtered
  7. concentrationconcentrated
  8. customThe oily residue was triturated with 1:1 ether-hexanes
  9. filtrationthe orange solid collected by filtration
  10. temperaturecooled
  11. filtrationfiltered

출처 및 근거

ORD 기록
ord-7ef99151d21b417ebb9d2095ffc9c011
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921756B2

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