Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | HCID 59331428 | HCID 59331428 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 59331506 | HCID 59331506 | 73.1% |
Reaction Steps
A mixture of (5E)-5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hex-5-ene-1,4-dione (4.79 g), ammonium acetate (3.40 g) and acetic acid (15 mL) was stirred at 90° C. for 2 hr. Water was added to the reaction mixture, and the mixture was neutralized with 8N aqueous sodium hydroxide solution. The precipitated solid was collected by filtration, washed with water, and dried. The obtained solid was dissolved in tetrahydrofuran, and the solution was treated with activated carbon and concentrated. Cold ethyl acetate was added to the obtained residue to allow crystallization. The crystals were collected by filtration, washed with cold ethyl acetate and dried to give the title compound (3.38 g, yield 73%) as pale-yellow crystals. melting point 196-197° C. MS: 523 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318746B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-d5f9aa1036f847a3bc3a0a3c0cd5aff9 |
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| Source note | uspto-grants-2012_11 |
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