Bromotrimethylsilane → HCID 68593442, compound

HRID 2191059Notes

Reaction equation

HRID 2191059 reaction equation
C([O:3][P:4]([CH:9]=[CH:10][CH:11]1[O:15][CH:14]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[NH:25][CH3:26])[CH:13]([O:27]C(=O)C2C=CC=CC=2)[CH2:12]1)([O:6]CC)=[O:5])C.C[Si](Br)(C)C>CC#N>[OH:27][CH:13]1[CH:14]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][C:21]=3[NH:25][CH3:26])[O:15][CH:11]([CH:10]=[CH:9][P:4](=[O:3])([OH:6])[OH:5])[CH2:12]1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 72247304HCID 72247304, compound

Product 1

HCID 68593442HCID 68593442, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 47.1 (277 mg, 0.45 mmol) was dissovled in 4.5 mL anhydrous CH3CN and treated with TMSBr (0.9 mL, 6.8 mmol). The solution was stirred at rt for 3 h, and then concentrated under reduced pressure. The residue was dissolved in NH4OH, stirred for another 2 h, and concentrated under reduced pressure. The residue was subjected to a reverse phase HPLC to give compound 47.2 (97 mg, 51% yield). 1H NMR (D2O, 300 MHz): δ 2.15-2.23 (m, 2H), 3.02 (s, 3H), 4.96 (s, 1H), 5.90-5.95 (m, 1H), 6.02 (d, 1H, J=1.2), 6.39 (m, 1H), 8.09 (s, 1H), 8.17 (s, 1H). 31PNMR: 11.34 ppm. LRMS [M−H]− C12H16N5O5P requires 340.1. Found 340.0.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in NH4OH
  3. stirringstirred for another 2 h
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1372a54474f9455a9c6ebd3b57509704
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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