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

HRID 1782178Notes

Reaction equation

HRID 1782178 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f52de335c6ce4011aaf0caf825dbf36c
Source dataset
uspto-grants-2009_03
Patent number
US07498353B2

Reaction notes

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