HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropyl Ether → 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(p-methoxy-phenylmethyl)-dihydrofuran-2-(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropyl Ether | HCID 7914 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate | HCID 10870461 | — |
| Reactant | p-Methoxybenzyl iodide | HCID 11746977 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(p-methoxy-phenylmethyl)-dihydrofuran-2-(3H)-one | HCID 67718528 | — |
Reaction Steps
2.98 g (9.74 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-dihydrofuran-2-(3H)-one dissolved in 40 ml of THF are deprotonated at -75° C. with 19.5 ml of lithium bis(trimethylsilyl)amide 1M in THF and alkylated with 2.9 g (11.7 mmol) of p-methoxybenzyl iodide in 20 ml of THF (45 min). Column chromatography (SiO2, hexane/ethyl acetate 2:1) and digestion using diisopropyl ether yield the pure title compound; TLC Rf (D)=0.32; tRet (I)=16.7 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05663168 |
| Source dataset | uspto-grants-1997_09 |
| ORD ID | ord-5f42dba7011f46a69403b94c869bbb64 |
| Source note | uspto-grants-1997_09 |