Trimethylsilyl iodide → HCID 58379622, compound

HRID 1630356Notes

Reaction equation

HRID 1630356 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[N:8][C:9]3[CH:10]=[CH:11][C:12]([C:15]4[CH:16]=[N:17][C:18]5[C:23]([CH:24]=4)=[CH:22][CH:21]=[CH:20][CH:19]=5)=[N:13][C:14]=3[C:5]=2[N:4]([CH:25]2[CH2:30][CH2:29][N:28](C(OCC3C=CC=CC=3)=O)[CH2:27][CH2:26]2)[C:3]1=[O:41].I[Si](C)(C)C>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:6]2[CH:7]=[N:8][C:9]3[CH:10]=[CH:11][C:12]([C:15]4[CH:16]=[N:17][C:18]5[C:23]([CH:24]=4)=[CH:22][CH:21]=[CH:20][CH:19]=5)=[N:13][C:14]=3[C:5]=2[N:4]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:3]1=[O:41]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 45254979HCID 45254979, compound

Product 1

HCID 58379622HCID 58379622, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a cooled (0° C.) yellow solution of compound 49 (5.0 g, 9.2 mL) in chloroform (130 mL) was added iodotrimethylsilane (TMSI) (9.0 mL, 64 mmol), dropwise, turning to an orange mixture. After 3 hours the reaction was quenched with methanol and concentrated. The resulting residue was slurried in diethyl ether and filtered solids, and the solids were washed with diethyl ether to remove all benzyl iodide. To the solids was then added 2 N sodium hydroxide (20 mL) and water (150 mL). With stirring the orange suspension slowly turned to a cream suspension. The solids were collected by filtration and purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0-10%) to afford Compound 118 (3.6 g, 96%).

Workup

  1. customAfter 3 hours the reaction was quenched with methanol
  2. concentrationconcentrated
  3. filtrationfiltered solids
  4. washthe solids were washed with diethyl ether
  5. customto remove all benzyl iodide
  6. additionTo the solids was then added 2 N sodium hydroxide (20 mL) and water (150 mL)
  7. filtrationThe solids were collected by filtration
  8. custompurified by flash chromatography
  9. washeluting with chloroform/7 N ammonia in methanol (0-10%)

Sources & evidence

ORD record
ord-c82b446f8b2041d2820f07bdc0b2cc07
Source dataset
uspto-grants-2014_07
Patent number
US08791131B2

Reaction notes

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