HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hexamethyldisilazide → HCID 56615310, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one | HCID 10946873 | — |
| Reactant | p-Benzyloxybenzyl iodide | HCID 11723738 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 56615310 | HCID 56615310 | — |
Reaction Steps
Analogously to Example 21 D) 1) c), 30.9 g (99.26 mmol) of 5(S)-[1(S)-(Boc-amino)-2-cyclohexylethyl]-dihydrofuran-2-(3H)-one are reacted with 200 ml (200 mmol) of lithium bis(trimethylsilyl)amide 1M in THF and 34 g (104.8 mmol) of 4-benzyloxybenzyl iodide to yield the title compound. The title compound is purified by column chromatography (SiO2, hexane/ethyl acetate: 4/1 to 1/1) and crystallisation (hexane/ethyl acetate); TLC Rf (C)=0.33; tRet (IV)=20.41 min; FAB-MS (M+H+)=508.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05643878 |
| Source dataset | uspto-grants-1997_07 |
| ORD ID | ord-93cccff67ca9429690db824b724300ec |
| Source note | uspto-grants-1997_07 |