Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 67495464 | HCID 67495464 | — |
| Product | HCID 67494873 | HCID 67494873 | — |
Reaction Steps
To a mixture of (R)-4-(5-carboxy-pyridin-2-yl)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (50 g, 0.156 mol) and methanol (500 mL) was slowly added concentrated sulfuric acid (37 mL). The reaction mixture was warmed to 64° C., stirred at 64° C. overnight, cooled to RT and then ice water (800 mL) was added followed by 50% aqueous sodium hydroxide (60 mL). The reaction mixture was extracted with ethyl acetate (3×800 mL). Combined organic layers were dried over sodium sulfate and evaporated to give the title intermediate as an oil. HPLC Method A: Retention time 3.50 and 3.72 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921372B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-a0fa2163309947f09869fdf04a5a6395 |
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| Source note | uspto-grants-2014_12 |
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