Hydrochloric Acid → (5R)-3-(4-Ethynyl-3-fluorophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

HRID 456797Notes

Reaction equation

HRID 456797 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][N:20]3[CH:24]=[CH:23][N:22]=[N:21]3)[O:16][C:15]2=[O:25])[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][Si](C)(C)C.[OH-].[K+].Cl>CO.C(Cl)Cl.O>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][N:20]3[CH:24]=[CH:23][N:22]=[N:21]3)[O:16][C:15]2=[O:25])=[CH:3][C:2]=1[F:1])#[CH:9]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58625197(5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one2×

Product 1

HCID 58625205(5R)-3-(4-Ethynyl-3-fluorophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-oneYield 47.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Intermediate 17, 6.1 g, 17 mmol) was stirred in methanol (155 ml). 1 N Potassium hydroxide (30 ml) was added and the reaction was stirred for 20 minutes. The solution was diluted with methylene chloride (200 ml) then acidified to pH 1.5 using 1 N hydrochloric acid. The solution was diluted with water and the compound was extracted using methylene chloride. The organic layer was washed with water, dried (magnesium sulfate), filtered, and concentrated. The orange solid was adsorbed onto silica gel and chromatographed using ethyl acetate to give the title compound as a yellow solid (2.3 g).

Workup

  1. extractionthe compound was extracted
  2. washThe organic layer was washed with water
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-2ddba926bbfd4ae8955acddc4c58f7db
Source dataset
uspto-grants-2007_03
Patent number
US07186738B2

Reaction notes

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