Methanesulfonyl chloride → 5(R)-Imidazol-2-ylthiomethyl-3-(4-[3,6-dihydro-(2H)-pyran-4-yl]-3-fluorophenyl)oxazolidin-2-one

HRID 1167500Notes

Reaction equation

N12CCCN=C1CCCCC2.CS(O[CH2:17][C@@H:18]1[O:22][C:21](=[O:23])[N:20]([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH2:31][CH2:32][O:33][CH2:34][CH:35]=3)=[C:26]([F:36])[CH:25]=2)[CH2:19]1)(=O)=O.CS(Cl)(=O)=O.[SH:42][C:43]1[NH:44][CH:45]=[CH:46][N:47]=1>O1CCOCC1>[NH:44]1[CH:45]=[CH:46][N:47]=[C:43]1[S:42][CH2:17][C@@H:18]1[O:22][C:21](=[O:23])[N:20]([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH2:31][CH2:32][O:33][CH2:34][CH:35]=3)=[C:26]([F:36])[CH:25]=2)[CH2:19]1

Participants

Conditions

Temperature: 60 °C

Procedure

1,8-Diazabicyclo[5,4,0]undec-7-ene (0.1 ml, 0.674 mmol) was added to a stirred suspension of 5(R)-methanesulfonyloxymethyl 3-(4-[3,6-dihydro-(2H)-pyran-4-yl]-3-fluorophenyl)oxazolidin-2-one (prepared from the 5(R)-hydroxymethyl compound (WO97/09328) by reaction with methylsulfonyl chloride) (0.25 g, 0.674 mmol) and 2-mercaptoimidazole (0.067 g, 0.674 mmol) in dioxan (2 ml) under nitrogen. The mixture was heated at 60° C. for 4 hours and evaporated. The residue was purified by column chromatography, eluting first with 2% MeOH/EtOAc and then with 4% MeOH/EtOAc to give the title product as a solid (0.077 g, 30%); mp 178-179° C. (dec.) MS: 476 (MH+); NMR: 2.39 (2H, bs); 3.42 (2H, m); 3.79 (2H, t); 3.86 (1H, m); 4.19 (3H, m); 4.89 (1H, m); 6.07 (1H, s); 7.04 (2H, s); 7.26 (1H, dd); 7.38 (1H, t); 7.46 (1H, d).

Workup

customevaporated
customThe residue was purified by column chromatography
washeluting first with 2% MeOH/EtOAc

Sources & evidence

ORD record: ord-aaa55f01bfd44671acd69fa83abf7112
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617339B1

Reaction notes

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