Trimethylsilyl iodide → HCID 46889774, compound

HRID 46202Notes

Reaction equation

[Cl:1][C:2]1[CH:20]=[CH:19][C:18]([C@H:21]2[C@H:26]([O:27]CC3C=CC=CC=3)[C@@H:25]([O:35]CC3C=CC=CC=3)[C@H:24]([O:43]CC3C=CC=CC=3)[C@@H:23]([CH2:51][O:52]CC3C=CC=CC=3)[O:22]2)=[CH:17][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8]([C:11]2[O:12][C:13]([CH3:16])=[CH:14][N:15]=2)=[CH:7][CH:6]=1.I[Si](C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:18]([C@H:21]2[C@H:26]([OH:27])[C@@H:25]([OH:35])[C@H:24]([OH:43])[C@@H:23]([CH2:51][OH:52])[O:22]2)=[CH:17][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8]([C:11]2[O:12][C:13]([CH3:16])=[CH:14][N:15]=2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-(6-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazin-3-yl)-5-methyloxazole (1.2 mmol) from Step 2 in acetonitrile (5 mL) was added Iodotrimethylsilane (3 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 (62 mg, 0.14 mmol, 11%) as a yellow solid.

Workup

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

Sources & evidence

ORD record: ord-a4f933002906477da2381c4258aed56a
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541380B2

Reaction notes

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