Pyridine → HCID 58758448, compound

HRID 459035Notes

Reaction equation

HRID 459035 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.N1C=CC=CC=1.[CH3:39][C:40](OC1C(=O)OC(=O)C1OC(C)=O)=[O:41]>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:40]([O:20][CH2:19][C@H:17]1[O:16][N:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]3[CH:6]=[CH:5][C:4]([N:21]4[CH2:25][C@H:24]([CH2:26][N:27]5[CH:31]=[CH:30][N:29]=[N:28]5)[O:23][C:22]4=[O:32])=[CH:3][C:2]=3[F:1])=[CH:9][N:10]=2)[CH2:18]1)(=[O:41])[CH3:39]

Participants

6

Reactant 3

HCID 1049PyridineHCID 954112,5-Dioxooxolane-3,4-diyl diacetateHCID 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 58758448HCID 58758448, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydro-3-isoxazolyl]-3-pyridinyl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 1, 200 mg, 0.46 mmol) was suspended in 2 mL of anhydrous dimethylformamide. Anhydrous pyridine (2 mL, 24 mmol), 4-dimethylaminopyridine (DMAP) (20 mg, 0.17 mmol) and di-O-acetyl-L-tartaric anhydride (210 mg, 0.97 mmol) were added and the solution was stirred for 16 hours at room temperature during which the mixture turned black. The reaction was quenched with 1 mL of methanol, the solvents evaporated in vacuo and the product isolated by flash chromatography on silica using a gradient from 0 to 5% methanol in dichloromethane to yield 50 mg (25%) of the title compound as an off white solid.

Workup

  1. customThe reaction was quenched with 1 mL of methanol
  2. customthe solvents evaporated in vacuo
  3. customthe product isolated by flash chromatography on silica using a gradient from 0 to 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-3579e985c66c4b689c84746083b3b2ca
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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