Water → HCID 44354895, compound

HRID 1167495Notes

Reaction equation

[H-].[Na+].[OH:3][CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH2:18][CH2:19][O:20][CH2:21][CH:22]=3)=[C:13]([F:23])[CH:12]=2)[CH2:6]1.C[C:25]1[O:26][C:27]([CH:30]=S(=O)=O)=[N:28][N:29]=1.O>CS(C)=O>[CH3:30][C:27]1[O:26][C:25]([O:3][CH2:4][C@@H:5]2[O:9][C:8](=[O:10])[N:7]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH2:18][CH2:19][O:20][CH2:21][CH:22]=4)=[C:13]([F:23])[CH:12]=3)[CH2:6]2)=[N:29][N:28]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Sodium hydride (28 mg of a 60% suspension in mineral oil, 0.69 mmol) was added to a solution of 5(R)-hydroxymethyl-3-(4-[3,6-dihydro-(2H)-pyran-4-yl]-3-fluorophenyl)oxazolidin-2-one (0.2 g, 0.69 mmol) in DMSO (5 ml) and the mixture was stirred for 1 hour. 2-Methyl-5-sulfonylmethyl-1,3,4-oxadiazole (RB Woodward et al, (Journal of the American Chemical Society 105, 904 [1983]) (0.11 g, 0.69 mmol) was added and the solution heated at 110° C. for 9 hours. Water (40 ml) was added and the mixture extracted three times with EtOAc. The combined extracts were dried by filtration through phase separation paper (Whatman 1PS) and evaporated. The residue was purified by flash column chromatography, eluting first with EtOAc and then with EtOAc/MeOH (20:1) to give the title product (23 mg, 9%) as a solid (mp 146-147° C.). MS: 376 (MH+).

Workup

extractionthe mixture extracted three times with EtOAc
customThe combined extracts were dried by filtration through phase separation paper (Whatman 1PS)
customevaporated
customThe residue was purified by flash column chromatography
washeluting first with EtOAc

Sources & evidence

ORD record: ord-db6f2db07cf84711bfe11fb7818ec7a1
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617339B1

Reaction notes

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