Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid | HCID 6993444 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | E-1210 | HCID 16719049 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59293922 | HCID 59293922 | 60.9% |
Reaction Steps
To a solution of 3-(3-(4-(pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine (900 mg, 2.5 mmol) described in Reference Example 1 in acetonitrile (15 mL) were added (S)-2-tert-butoxycarbonylamino-pentanedioic acid 1-tert-butyl ester (860 mg, 2.8 mmol), triethylamine (0.37 mL, 2.6 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate (1.1 g, 2.8 mmol) at 0° C., which was stirred overnight at 60° C. Water and ethyl acetate were added to the reaction solution, and the organic layer was washed with saturated brine. The residue thus obtained was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1), so as to obtain the titled compound (980 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08188119B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-5122496f1d414711a415778376309b51 |
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| Source note | uspto-grants-2012_05 |
|---|
