Water → HCID 86613472, compound

HRID 1966929Notes

Reaction equation

C[Sn](C)(C)[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][C@H:12]([CH2:14][C:15](=[O:19])[C:16]([NH2:18])=[O:17])[O:11][CH2:10]2)=[CH:5][C:4]=1[F:20].[O:23]=[C:24]1[CH2:28][CH:27]([CH2:29][OH:30])[CH2:26][N:25]1[C:31]1[CH:36]=[CH:35][C:34](Br)=[CH:33][N:32]=1.[Cl-].[Li+].O>CN1CCCC1=O>[O:23]=[C:24]1[CH2:28][CH:27]([CH2:29][OH:30])[CH2:26][N:25]1[C:31]1[CH:36]=[CH:35][C:34]([C:3]2[CH:8]=[CH:7][C:6]([N:9]3[CH2:13][C@H:12]([CH2:14][C:15](=[O:19])[C:16]([NH2:18])=[O:17])[O:11][CH2:10]3)=[CH:5][C:4]=2[F:20])=[CH:33][N:32]=1

Participants

Conditions

Temperature: 110 °C

Procedure

In 14 ml of 1-methyl-2-pyrrolidone was dissolved 1.8 g of (S)-3-(4-trimethylstannyl-3-fluorophenyl)-2-oxo-5-oxazolidinylmethyl acetamide. The solution was added 1.03 g of 2-(2-oxo-4-hydroxymethylpyrrolidin-1-yl)-5-bromopyridine, 0.55 g of lithium chloride and 0.15 g of dichlorobistriphenylphosphine palladium (II) at room temperature and then stirred at the temperature of 110° C. for 2 hours. The reaction mixture was added with water and extracted with ethyl acetate. After being washed with brine, the organic layer, thus separated, was dehydrated, filtered, concentrated in vacuo and purified by column chromatography thereby to obtain (S)-3-(4-(2-(2-oxo-4-hydroxymethylpyrrolidin-1-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinylmethyl acetamide 410 mg. Yield 21%.

Workup

extractionextracted with ethyl acetate
washAfter being washed with brine
customthe organic layer, thus separated
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by column chromatography

Sources & evidence

ORD record: ord-da740737ba52424c9ffa1295c959949b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420676B2

Reaction notes

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