Sodium methanesulfinate → {3-[4-Methanesulfonyl-2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid methyl ester

HRID 885318Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:35])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][C:15]=2[CH2:21][N:22]2[C@@H:26]([CH3:27])[C@@H:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:24][C:23]2=[O:34])[CH:6]=1.[CH3:36][S:37]([O-:39])=[O:38].[Na+]>CN1C(=O)CCC1.[Cu](I)I>[CH3:1][O:2][C:3](=[O:35])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][C:14]2[CH:19]=[CH:18][C:17]([S:37]([CH3:36])(=[O:39])=[O:38])=[CH:16][C:15]=2[CH2:21][N:22]2[C@@H:26]([CH3:27])[C@@H:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:24][C:23]2=[O:34])[CH:6]=1

Participants

Conditions

Temperature: 150 °C

Procedure

{3-[4-Bromo-2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid methyl ester (0.1 g, 0.19 mmol), sodium methanesulfinate (0.087 g, 0.84 mmol), and copper iodide (0.159 g, 0.84 mmol) were combined in NMP (2 mL) and degassed with N2 for 10 minutes. The reaction was then stirred at 150° C. for 3 hours, until no starting material was seen by analytical tlc. The mixture was filtered through Celite and worked-up with brine and EtOAc, and the crude material was purified by silica gel chromatography to give the desired product as a colorless oil (0.1 g).

Workup

customdegassed with N2 for 10 minutes
filtrationThe mixture was filtered through Celite
customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record: ord-907f8b68cf2c4c57bb5f964b65631520
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242145B2

Reaction notes

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