HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Water → 1-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Water | HCID 962 | — |
| Edukt | L-Hydroxyproline | HCID 5810 | — |
| Edukt | Benzyl chloroformate | HCID 10387 | — |
| Edukt | Sodium Bicarbonate | HCID 516892 | — |
| Lösungsmittel | Acetone | HCID 180 | — |
| Produkt | 1-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate | HCID 391517 | 101,8% |
Reaktionsschritte
Benzyl chloroformate (8.6 mL, 0.06 mol) was dissolved in acetone (12 mL), and this solution was added dropwise to a stirred solution of trans-4-Hydroxy-L-proline (6.56 g, 0.05 mol) in satd. NaHCO3 (160 mL) and H2O (24 mL). The resulting solution was stirred for 6 h at room temperature. The solution was washed with diethyl ether, and the organic layer was discarded. The aqueous layer was acidified with to pH 3 with 1 M HCl and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated to afford 13.5 g (quantitative yield) of the desired product as an oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06710186B2 |
| Quelldatensatz | uspto-grants-2004_03 |
| ORD ID | ord-9a1d1d93f4d949d09dae036b0adc2a31 |
| Quellennotiz | uspto-grants-2004_03 |