Trimethylsilyl iodide → HCID 86626607, compound

HRID 349456Notes

Reaction equation

HRID 349456 reaction equation
C[O:2][P:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[N:19]=[N:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[C:27][CH2:28][C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[CH:21]=3)=[N:16]2)=[CH:10][CH:9]=1)(=[O:6])[O:4]C.C[Si](I)(C)C>C(Cl)Cl>[F:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][C:27]#[C:26][C:22]2[CH:21]=[C:20]([C:17]3[N:18]=[N:19][N:15]([CH2:14][C:11]4[CH:10]=[CH:9][C:8]([CH2:7][P:3](=[O:2])([OH:6])[OH:4])=[CH:13][CH:12]=4)[N:16]=3)[CH:25]=[CH:24][CH:23]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86626608HCID 86626608, compound

Product 1

HCID 86626607HCID 86626607, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [4-(5-{3-[3-(4-fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl)benzyl] phosphonic acid dimethyl ester (0.25 g, 0.53 mmol) in methylene chloride (15 mL) was cooled to 0° C., then treated with trimethylsilyliodide (0.23 mL, 1.33 mmol). The reaction mixture was removed from the cooling bath and stirred at room temperature for 1 hour. The reaction mixture was concentrated on the rotary evaporator without heat and the residue was treated with chloroform. The resulting solid was collected by filtration, washed with chloroform, triturated with hot ether, collected by filtration and dried. High performance liquid chromatography (“HPLC”) indicates that this solid is 65% pure.

Workup

  1. customThe reaction mixture was removed from the cooling bath
  2. concentrationThe reaction mixture was concentrated on the rotary evaporator
  3. temperaturewithout heat
  4. additionthe residue was treated with chloroform
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with chloroform
  7. customtriturated with hot ether
  8. filtrationcollected by filtration
  9. customdried

Sources & evidence

ORD record
ord-67efa58a9006414dbf79051ec8887798
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

Loading…