Trimethylsilyl iodide → HCID 46229217, compound

HRID 46195Notes

Reaction equation

HRID 46195 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([CH:20]2[C@H:25]([O:26]CC3C=CC=CC=3)[C@@H:24]([O:34]CC3C=CC=CC=3)[C@H:23]([O:42]CC3C=CC=CC=3)[C@@H:22]([CH2:50][O:51]CC3C=CC=CC=3)[O:21]2)=[CH:16][C:3]=1[CH2:4][C:5]1[S:6][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[N:8][N:9]=1.I[Si](C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([CH:20]2[C@H:25]([OH:26])[C@@H:24]([OH:34])[C@H:23]([OH:42])[C@@H:22]([CH2:50][OH:51])[O:21]2)=[CH:16][C:3]=1[CH2:4][C:5]1[S:6][C:7]([C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)=[N:8][N:9]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 67287138HCID 67287138, compound

Product 1

HCID 46229217HCID 46229217, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-5-(pyridin-4-yl)-1,3,4-thiadiazole (2.83 mmol) from Step 1 in acetonitrile (5 mL) was added Iodotrimethylsilane (5 mL). The resulting reaction mixture was heated to 50° C. overnight. After cooling to 0° C., the reaction quenched with methanol and concentrated in vacuo. Purification by reverse phase preparative HPLC (Gilson®, SunFire™ Prep, 5 to 50% acetonitrile in water gradient) provided the title compound (139 mg, 0.31 mmol, 11%, mixture of α,β-anomer) as a yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling to 0° C.
  3. customthe reaction quenched with methanol
  4. concentrationconcentrated in vacuo
  5. customPurification by reverse phase preparative HPLC (Gilson®, SunFire™ Prep, 5 to 50% acetonitrile in water gradient)

Sources & evidence

ORD record
ord-4d69aae9f76c43c793ec07c0e13e3550
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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