Trimethylsilyl iodide → HCID 178456034, compound

HRID 1048598Notes

Reaction equation

HRID 1048598 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH2:30][CH3:31])[CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][S:24]3(=[O:29])=[O:28])[C:11](=[O:32])[C@H:10]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([O:40]C)[N:35]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.I[Si](C)(C)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)[N:12]([C@@H:21]([CH2:30][CH3:31])[CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][S:24]3(=[O:29])=[O:28])[C:11](=[O:32])[C@H:10]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([OH:40])[N:35]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 58573946HCID 58573946, compound

Product 1

HCID 178456034HCID 178456034, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To the product of Example 420, Step C (0.05 g, 0.081 mmol) in chloroform (1.622 ml) was added iodotrimethylsilane (0.046 ml, 0.324 mmol). The reaction was warmed to 50° C. After 4 hours, the reaction was quenched with saturated bicarbonate (10 mL) and extracted with dichloromethane (2×15 mL) and 5% MeOH in CH2Cl2 (1×15 mL). The combined organics were dried with sodium sulfate and concentrated in vacuo. Silica gel chromatography (0.5 to 7.5% MeOH in dichloromethane) afforded the title compound.

Workup

  1. customthe reaction was quenched with saturated bicarbonate (10 mL)
  2. extractionextracted with dichloromethane (2×15 mL) and 5% MeOH in CH2Cl2 (1×15 mL)
  3. dry with materialThe combined organics were dried with sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e405daac392043efa2025c25b9df8138
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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