Tetrahydrofuran → HCID 22862181, compound

Temperature

-78 °C

BuLi (1.6M solution in hexanes, 4.4 mmol, 2.75 ml, 1.2 equiv.) was added dropwise to a solution of (S)-4-(phenylmethyl)-2-oxazolidinone (3.64 mmol, 0.64 g) in THF (15 ml) at -78° C., under N2 atmosphere. The orange solution was stirred for 30 mins at -78° C. and then a solution of p-toylvalerylchloride (4.06 mmol, 0.86 g) in THF (5 ml) was added dropwise. The reaction mixture was stirred at -78° C. for 2 hrs before quenching at -78° C. with a mixture of brine and 10% aqueous HCl (1:1, 20 ml). On warming to ambient temperature the reaction mixture was partitioned between EtOAc and water. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were washed once with brine, once with sodium bicarbonate solution and dried over MgSO4. The solvent was removed under vacuum to give a brown oil which was purified on silica gel (Merck 9385) eluting with 20% EtOAc/hexane to give the compound as a slightly yellow oil (0.65 g, 51%).

1. stirringThe reaction mixture was stirred at -78° C. for 2 hrs
2. custombefore quenching at -78° C. with a mixture of brine and 10% aqueous HCl (1:1, 20 ml)
3. temperatureOn warming to ambient temperature the reaction mixture
4. customwas partitioned between EtOAc and water
5. customThe aqueous layer was separated
6. extractionextracted twice with EtOAc
7. washThe combined organic layers were washed once with brine, once with sodium bicarbonate solution
8. dry with materialdried over MgSO4
9. customThe solvent was removed under vacuum
10. customto give a brown oil which
11. customwas purified on silica gel (Merck 9385)
12. washeluting with 20% EtOAc/hexane

ORD record

ord-d1dc3b5cf76c4178a8ddb651ba1b4994

Source dataset

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05530128