Hydrochloric Acid → 5-Chloro-N-[((5S)-3-{4-[3-(2-hydroxyethyl)-2-oxopyridin-1(2H)-yl]-3-methylphenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]thiophene-2-carboxamide

HRID 452247Notes

Reaction equation

HRID 452247 reaction equation
Cl.[Si]([O:19][CH2:20][CH2:21][C:22]1[C:23](=[O:51])[N:24]([C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:38][C@H:37]([CH2:39][NH:40][C:41]([C:43]4[S:44][C:45]([Cl:48])=[CH:46][CH:47]=4)=[O:42])[O:36][C:35]3=[O:49])=[CH:30][C:29]=2[CH3:50])[CH:25]=[CH:26][CH:27]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>CO.ClCCl>[Cl:48][C:45]1[S:44][C:43]([C:41]([NH:40][CH2:39][C@@H:37]2[O:36][C:35](=[O:49])[N:34]([C:31]3[CH:32]=[CH:33][C:28]([N:24]4[CH:25]=[CH:26][CH:27]=[C:22]([CH2:21][CH2:20][OH:19])[C:23]4=[O:51])=[C:29]([CH3:50])[CH:30]=3)[CH2:38]2)=[O:42])=[CH:47][CH:46]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59410172HCID 59410172, compound

Product 1

HCID 251438325-Chloro-N-[((5S)-3-{4-[3-(2-hydroxyethyl)-2-oxopyridin-1(2H)-yl]-3-methylphenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]thiophene-2-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

With ice-cooling, 400 ml of 1.25N hydrochloric acid in methanol are added to 43.8 g (60.3 mmol) of the compound from Example 27A. After 1 h, the mixture is diluted with dichloromethane, and the aqueous phase is then removed. The organic phase is washed twice with water, dried over sodium sulphate and, after filtration, concentrated to dryness under reduced pressure. The residue is applied to silica gel and chromatographed using a gradient of cyclohexane and ethyl acetate. The product-containing fractions are combined and concentrated to dryness under reduced pressure. This gives 19.6 g (66% of theory) of the desired product.

Workup

  1. temperatureWith ice-cooling
  2. customthe aqueous phase is then removed
  3. washThe organic phase is washed twice with water
  4. dry with materialdried over sodium sulphate
  5. filtrationafter filtration
  6. concentrationconcentrated to dryness under reduced pressure
  7. customchromatographed
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-94019b14ff04487da07f34b4de8e8839
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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