HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzonitrile, 3-(bromomethyl)- → 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(m-cyanophenylmethyl)-dihydrofuran-2-(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzonitrile, 3-(bromomethyl)- | HCID 97249 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate | HCID 10870461 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(m-cyanophenylmethyl)-dihydrofuran-2-(3H)-one | HCID 67718959 | — |
Reaction Steps
Analogously to Example 21 D) 1)c), 2.0 g (6.55 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-dihydrofuran-2-(3H)-one [Example 21 D) 1)b)] dissolved in 40 ml of THF are deprotonated at -75° C. with 13.1 ml of lithium bis(trimethylsilyl)amide 1M in THF and alkylated (60 min -60° C.) with 1.4 g (7.2 mmol) of 3-bromomethylbenzonitrile (Fluka; Buchs/Switzerland). Column chromatography (SiO2, hexane/ethyl acetate 2:1) and stirring in hexane yields the pure title compound: TLC Rf (D)=0.41; tRet (I)=16.1 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05643878 |
| Source dataset | uspto-grants-1997_07 |
| ORD ID | ord-da8c9f7972794e2d8ba9f3b6d3fcf448 |
| Source note | uspto-grants-1997_07 |