Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Chlorotrimethylsilane | HCID 6397 | — |
| Reactant | N-(3,4-Dimethyl-5-isoxazolyl)-2′-[hydroxy(5-phenyl-2-oxazolyl)methyl]-N-[(2-methoxyethoxy)methyl]-4′-(2-oxazolyl)[1,1′-biphenyl]-2-sulfonamide | HCID 22103475 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 22103733 | HCID 22103733 | — |
Reaction Steps
To a solution of the title compound of Step (B) (200 mg, 0.305 mmol) in 10.2 ml of CH3CN, Me3SiCl (199 mg, 1.83 mmol) was added and followed by NaI (274 mg, 1.83 mmol). The mixture was stirred at room temperature for 1 hr. Additional Me3SiCl (199 mg, 1.83 mmol) and NaI (274 mg, 1.83 mmol) were added in three portions and the reaction was stirred for additional 5.5 hr. The mixture was added to 5 ml H2O and 50 ml EtOAc. The organic layer was washed with sat. Na2S2 O3, brine, dried and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 27% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 73% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (65 mg, 37%) as a white solid, m.p. 125°-135° C. (amorphous).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05846990 |
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| Source dataset | uspto-grants-1998_12 |
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| ORD ID | ord-09765838cc434195b83161283124a2c8 |
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| Source note | uspto-grants-1998_12 |
|---|
