Hydrochloric Acid → (5R)-3-(4-Ethynyl-3-fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 1371833Notes

Reaction equation

HRID 1371833 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]=[C:23]([CH3:25])[N:22]=[N:21]3)[O:16][C:15]2=[O:26])[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][Si](C)(C)C.[OH-].[K+].Cl>CO>[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]=[C:23]([CH3:25])[N:22]=[N:21]3)[O:16][C:15]2=[O:26])=[CH:3][C:2]=1[F:1])#[CH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58626908(5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one2×

Product 1

HCID 58626911(5R)-3-(4-Ethynyl-3-fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-oneYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (Intermediate 10, 1.4 g, 3.76 mmol) was dissolved in methanol (10 ml) and cooled to 0° C. 1N potassium hydroxide aqueous solution (4 mL) was added and the mixture was stirred for one hour. 2M HCl (4 mLl) was added and the reaction mixture was stirred for 30 minutes. It was extracted with dichloromethane (30 mL), the organic phase was concentrated to dryness. The product was preciptitated from dichloromethane (10 mL) by the additon of hexanes (50 mL) to give the product as a colourless solid (0.91 g).

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes
  2. extractionIt was extracted with dichloromethane (30 mL)
  3. concentrationthe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-b3006ba2b64d4ee5b0cea97b5b5df0f3
Source dataset
uspto-grants-2007_01
Patent number
US07157482B2

Reaction notes

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