HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → (R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Citrate | HCID 31348 | — |
| Reactant | Ammonium Sulfate | HCID 6097028 | — |
| Reactant | Ethyl 3-(((benzyloxy)carbonyl)amino)-2,5-dioxopyrrolidine-3-carboxylate | HCID 10267979 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | (R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide | HCID 9944916 | 48% |
Reaction Steps
5.0 g of 2-benzyloxycarbonylamino-2-ethoxycarbonyl succinimide were dissolved in 100 g of dimethylsulfoxide and thereto, 100 g of 0.05 mol/L citrate buffer solution (pH 4.4) were added, followed by adjusting pH value of the resultant mixture to 6.5 with a 5% sodium hydroxide aqueous solution. Thereto, 0.28 mL of esterase (PLE (2.7 kU/mL); manufactured by BioCatalytics, Inc., ammonium sulfate suspension) were added and the resultant mixture was stirred at 25° C. for 78 hours, followed by analyzing quantitatively the reaction mixture. As a result, in the reaction mixture, 2.4 g (quantitative yield: 48.6%) of (R)-2-benzyloxycarbonylamino-2-ethoxycarbonyl succinimide having an optical purity of 97-5% e.e. were contained
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07994342B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-1d3648cab4ec4799a02fa82aadd1515a |
| Source note | uspto-grants-2011_08 |