HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propionic Acid → HCID 86754404, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propionic Acid | HCID 1032 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate | HCID 10870461 | — |
| Reactant | 2-{[4-(Bromomethyl)benzene-1-sulfonyl]methyl}-1,3-dichlorobenzene | HCID 22269428 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | 2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- | HCID 81646 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | HCID 86754404 | HCID 86754404 | — |
Reaction Steps
In analogy with Example 5d), 5.0 g (16.34 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]dihydrofuran-2-(3H)-one, dissolved in 24 ml of abs. THF and 2.7 ml of DMPU, are deprotonated, at -75° C., with 32.7 ml of a 1 M solution of lithium bis(trimethylsilyl)amide in THF, and alkylated, at -75° C., with 9.67 g (24.5 mmol) of p-(2,6-dichlorobenzylsulfonyl)benzyl bromide (Maybridge; Tintagel/UK) in 50 ml of abs. THF. Protonation, at -75° C., with 6.1 ml (81.7 mmol) of propionic acid and 6.1 ml of water, extraction and column chromatography (SiO2, hexane/ethyl acetate, 2:1) of the crude product, and crystallization from DIPE, affords the title compound: TLC Rf (D)=0.30; tRet (II)=17.3 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05935976 |
| Source dataset | uspto-grants-1999_08 |
| ORD ID | ord-568a6b3de37a411c9e7bc3037a178e68 |
| Source note | uspto-grants-1999_08 |