Bromotrimethylsilane → 2-(2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamido)ethylphosphonic acid

HRID 1782178노트

반응식

HRID 1782178 반응식
[Cl:1][CH:2]([Cl:35])[C:3]([N:5]([CH2:25][CH2:26][P:27](=[O:34])([O:31]CC)[O:28]CC)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[CH:13]=2)[CH:7]=1)=[O:4].Br[Si](C)(C)C>C(Cl)Cl>[Cl:35][CH:2]([Cl:1])[C:3]([N:5]([CH2:25][CH2:26][P:27](=[O:28])([OH:34])[OH:31])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:18]([Cl:24])=[CH:19][CH:20]=[CH:21][C:22]=3[Cl:23])[CH:13]=2)[CH:7]=1)=[O:4]

참가 물질

4

반응물 2

HCID 76113BromotrimethylsilaneHCID 57588307diethyl 2-(2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamido)ethylphosphonate

생성물 1

HCID 575884232-(2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamido)ethylphosphonic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diethyl 2-(2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamido)ethylphosphonate (Cpd. No. 1, 50 mg, 0.09 mmol) was dissolved in anhydrous methylene chloride (1 mL). Bromotrimethylsilane (750 μL, 5.7 mmol) was added and the mixture was stirred for 4 h whereupon the LC-MS confirmed the starting material was consumed. The solvent was removed under reduced pressure. The resulting residue was dissolved in methanol:water (1:1, 3 mL) and shaken for 30 min. The mixture was filtered over a pad of Celite. The Celite was washed with ethyl acetate. The combined filtrates were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-(2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamido)ethylphosphonic acid (Cpd. No. 2) as a white solid. 1H NMR (DMSO-d6): 8.02 (m, 2H), 7.69-7.56 (m, 5H), 7.38 (s, 1H), 6.33 (s, 1H), 3.86 (m, 2H), 1.83 ppm (m, 1H). MW=524 confirmed by LC-MS, tr=11.24 min (Method Y) MH+=522-526.

후처리

  1. customwas consumed
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe resulting residue was dissolved in methanol:water (1:1, 3 mL)
  4. stirringshaken for 30 min
  5. filtrationThe mixture was filtered over a pad of Celite
  6. washThe Celite was washed with ethyl acetate
  7. washThe combined filtrates were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f52de335c6ce4011aaf0caf825dbf36c
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498353B2

반응 노트

불러오는 중…