Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 2-Ethoxy-4-(3-((S)-3-methy-1-(2-piperidin-1-yl-phenyl)-butylamino)-2-oxo-propyl)-benzoic acid ethyl ester | HCID 10648419 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | Repaglinide | HCID 65981 | 83.2% |
Reaction Steps
Ethyl (S)-2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-amino carbonylmethyl]-benzoate (4.5 g, 0.0093 mol) was dissolved in methanol (45 ml), followed by the addition of sodium hydroxide solution (0.75 g of sodium hydroxide dissolved in 6 ml water). The reaction mixture was heated at 60-65° C. for 3-4 hours. Methanol (80-85%) was removed from the reaction mixture under vacuum. The remaining reaction mixture was diluted with water (45 ml) and pH was adjusted to 6.5-7.0 with 1N HCl. The precipitated solid was stirred for 2-3 hours followed by filtration and washing with water (45 ml). The product was further dried at 50-55° C. under vacuum for 6-8 hours to produce Repaglinide (Yield=83.2%; HPLC Purity: 99.89%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08101769B2 |
|---|
| Source dataset | uspto-grants-2012_01 |
|---|
| ORD ID | ord-281ce03874f640e88c967d90904e61fe |
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| Source note | uspto-grants-2012_01 |
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