Pyridine → (5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-[(methanesulfonyl)methyl]-oxazolidin-2-one

HRID 1452579Notes

Reaction equation

HRID 1452579 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19]O)[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[N:11][C:10]([CH3:13])=[N:9]1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].N1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][S:30]([CH3:29])(=[O:32])=[O:31])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[N:11][C:10]([CH3:13])=[N:9]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 57526987(5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one2×

Product 1

HCID 68877351(5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-[(methanesulfonyl)methyl]-oxazolidin-2-oneYield 44.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one (Intermediate 25) (10.08 g, 34.5 mmol) in dichloromethane (100 ml) and triethylamine (6.0 ml, 43 mmol) was cooled to 0° C. and methanesulfonyl chloride (3.2 ml, 41 mmol) was added by syringe. The reaction mixture was allowed to warm to room temperature overnight. More pyridine (50 ml) was added and the reaction mixture was cooled to 0° C. before adding additional methanesulfonyl chloride (3.2 ml, 41 mmol). The reaction was allowed to warm to room temperature and the solid was collected by filtration and washed with ethyl acetate to afford the crude title compound (5.49 g).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. filtrationthe solid was collected by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-56a5d0a3af874a2ba8c508fd039e0ee9
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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