Trimethylsilyl iodide → HCID 9796603, compound

HRID 970063Notes

Reaction equation

HRID 970063 reaction equation
C(OC([NH:11][CH:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:13][CH2:14][P:15](=[O:22])([O:19]CC)[O:16]CC)=O)C1C=CC=CC=1.I[Si](C)(C)C>C(Cl)Cl>[NH2:11][CH:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:13][CH2:14][P:15](=[O:16])([OH:22])[OH:19]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86598012HCID 86598012, compound

Product 1

HCID 9796603HCID 9796603, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 100 mg (0.2 mmol) of (±)-diethyl 3-(benzyloxycarbonylamino)pentadecylphosphate (from Example 27, Step C) in 1 mL of CH2Cl2 was treated with 0.11 mL (0.8 mmol) of iodotrimethylsilane then stirred at rt for 1 h. The reaction was quenched with 1 mL of methanol, stirred at rt for 15 min then concentrated. The resulting oil was dissolved in 0.5 mL of EtOAc, diluted with 5 mL of hexanes and. sonicated for 1 min. The suspension was filtered and dried to give 68 mg of the title compound: 1H NMR (500 MHz) δ 3.22-3.30 (m, 1H), 1.76-2.01 (m, 4H), 1.56-1.70 (m, 2H), 1.26-1.46 (m, 20H), 0.89 (t, J=6.9 Hz, 3H); ESI-MS 308.2 (M+H).

Workup

  1. customThe reaction was quenched with 1 mL of methanol
  2. stirringstirred at rt for 15 min
  3. concentrationthen concentrated
  4. dissolutionThe resulting oil was dissolved in 0.5 mL of EtOAc
  5. additiondiluted with 5 mL of hexanes
  6. customsonicated for 1 min
  7. filtrationThe suspension was filtered
  8. customdried

Sources & evidence

ORD record
ord-c93ce626e32f4617b486cd3d02239297
Source dataset
uspto-grants-2007_12
Patent number
US07309721B2

Reaction notes

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