Pyridine → HCID 58758456, compound

HRID 459039Notes

Reaction equation

HRID 459039 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][C@H:24]([CH2:26][N:27]3[CH:31]=[CH:30][N:29]=[N:28]3)[O:23][C:22]2=[O:32])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH2:18][C@@H:17]([CH2:19][OH:20])[O:16][N:15]=2)=[CH:12][CH:13]=1.[O:33]1[C:37](=[O:38])[CH2:36][CH2:35][C:34]1=[O:39].CN(C=O)C.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.CCOCC>[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][C@H:24]([CH2:26][N:27]3[CH:31]=[CH:30][N:29]=[N:28]3)[O:23][C:22]2=[O:32])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH2:18][C@@H:17]([CH2:19][O:20][C:37](=[O:38])[CH2:36][CH2:35][C:34]([OH:39])=[O:33])[O:16][N:15]=2)=[N:10][CH:9]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 7922Succinic anhydrideHCID 9932836(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Product 1

HCID 58758456HCID 58758456, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 1: 150 mg, 0.342 mmol), dihydrofuran-2,5-dione (83 mg, 0.83 mmol), and 4-dimethylaminopyridine (10.5 mg, 0.09 mmol) were added to DMF (2.5 ml) and pyridine (0.5 ml). The reaction was allowed to stir overnight at room temperature followed by addition to Et2O (100 ml). The precipitate was collected by filtration and washed with additional Et2O (2×20 ml). The precipitate was then suspended in CH2Cl2 (20 ml) and the precipitate was collected by filtration and then washed with additional CH2Cl2 (2×20 ml) to yield the product as a white solid (131 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with additional Et2O (2×20 ml)
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with additional CH2Cl2 (2×20 ml)

Sources & evidence

ORD record
ord-d8d5f6909a9d42dca945fc4afe484978
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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