HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propionic Acid → 5(S)-[1(S)-(Boc-Amino)-2-(p-benzyloxyphenyl)-ethyl]-3(R)-[(4-biphenylyl)methyl]dihydrofuran-2-(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propionic Acid | HCID 1032 | — |
| Reactant | 1,1'-Biphenyl, 4-(bromomethyl)- | HCID 257716 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | [(S)-2-(4-Benzyloxy-phenyl)-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester | HCID 54401688 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- | HCID 81646 | — |
| Product | 5(S)-[1(S)-(Boc-Amino)-2-(p-benzyloxyphenyl)-ethyl]-3(R)-[(4-biphenylyl)methyl]dihydrofuran-2-(3H)-one | HCID 70149090 | — |
Reaction Steps
In analogy with Example 5d), 5.55 g (13.5 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-benzyloxyphenyl)ethyl]dihydrofuran-2-(3H)-one [preparation, see Example 1g)], dissolved in 20 ml of THF and 2.3 ml of DMPU, are deprotonated, at -70° C., with 27 ml of a 1 M solution of lithium bis(trimethylsilyl)amide in THF, and alkylated (1 h) with 5.0 g (20.2 mmol) of 4-biphenylylmethyl bromide (Salor, Milwaukee, USA) in 16 ml of THF. Protonating with 5 ml (67.4 mmol) of propionic acid and 5 ml of water, at -75° C., extracting and medium pressure chromatography (gradient: 30-50% ethyl acetate in toluene) results in the title compound: TLC Rf (Q)=0.15; tRet (II)=20.0 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05935976 |
| Source dataset | uspto-grants-1999_08 |
| ORD ID | ord-f83b3b8f6a644818b23b812bab3d4c14 |
| Source note | uspto-grants-1999_08 |