Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Trimethylphosphine | HCID 68983 | — |
| Reactant | HCID 86656161 | HCID 86656161 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67301966 | HCID 67301966 | — |
Reaction Steps
To a stirred solution of 5-(1-azidoethyl)-4-(3-fluorophenyl)-2-methyl-1,3-benzothiazole (0.088 g, 0.28 mmol) in tetrahydrofuran (0.8 mL) and water (0.203 mL) was added 1.00 M of trimethylphosphine in tetrahydrofuran (0.338 mL, 0.338 mmol) at room temperature and the mixture was stirred at room temperature for 1 hour. To the mixture was added EtOAc and the mixture was extracted with 1 N HCl two times. The combined extracts were neutralized with solid sodium bicarbonate, and extracted with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue, showing two peaks with the same desired mass, was used directly in next step (74 mg, 91%). LCMS calculated for C16H16FN2S(M+H)+: m/z=287.1; found: 287.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680108B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-c06dd7f0266e464bb3a3b006077b8f74 |
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| Source note | uspto-grants-2014_03 |
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