Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Veratrylamine | HCID 79832 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | HCID 43610334 | HCID 43610334 | — |
| Product | HCID 67495123 | HCID 67495123 | 85.1% |
Reaction Steps
A mixture of 5.8 g of the compound obtained in Step 6.1, 7.02 g of DIEA and 12.38 g of HBTU is stirred for 30 minutes at room temperature. 4.37 g of veratrylamine are then added and the resulting mixture is stirred overnight at room temperature. The resulting mixture is evaporated under reduced pressure and the residue is taken up in EtOAc. This solution is washed with water and then sequentially with 1N HCl solution, with water, with saturated NaHCO3 solution, with water and with saturated NaCl solution. The resulting solution is dried over Na2SO4 and filtered, and the solvent is evaporated off under reduced pressure. The residue is chromatographed on silica gel, eluting with an EtOAc/heptane mixture from (50/50, v/v) to (70/30, v/v) to give 7.7 g of the expected product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08722659B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-216b4b71aa8a48e9876208860a8413c5 |
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| Source note | uspto-grants-2014_05 |
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