Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Sodium Tartrate | HCID 9357 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 68312845 | HCID 68312845 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68312658 | HCID 68312658 | 46% |
Reaction Steps
To a suspension of LiAlH4 (15 mg, 0.389 mmol) in THF (2 mL) was added a solution of 2-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-2-phenylmalonic acid diethyl ester (72.5 mg, 0.13 mmol) in THF (1 mL). The mixture was stirred at RT for 2 h, then EtOAc (5 mL) was added and stirring was continued for 10 min. An aqueous solution of Rochelle's salt was then added and stirring continued for a further 30 min. The mixture was filtered through a Celite® pad and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 4-12% MeOH in DCM) affording the title compound (28.1 mg, 46%). LCMS (Method B): RT 2.75 min [M+H]+ 476
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09090628B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-95563d459abf45ec86272062fc0fe9d2 |
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| Source note | uspto-grants-2015_07 |
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