HCID 59410177, compound → 5-Chloro-N-{[(5S)-3-{4-[3-(2-hydroxyethyl)-2-oxopyridin-1(2H)-yl]-3-methoxyphenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide

HRID 391734Notes

Reaction equation

HRID 391734 reaction equation
[Si]([O:18][CH2:19][CH2:20][C:21]1[C:22](=[O:51])[N:23]([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:37][C@H:36]([CH2:38][NH:39][C:40]([C:42]4[S:43][C:44]([Cl:47])=[CH:45][CH:46]=4)=[O:41])[O:35][C:34]3=[O:48])=[CH:29][C:28]=2[O:49][CH3:50])[CH:24]=[CH:25][CH:26]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>Cl.CO>[Cl:47][C:44]1[S:43][C:42]([C:40]([NH:39][CH2:38][C@@H:36]2[O:35][C:34](=[O:48])[N:33]([C:30]3[CH:31]=[CH:32][C:27]([N:23]4[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][CH2:19][OH:18])[C:22]4=[O:51])=[C:28]([O:49][CH3:50])[CH:29]=3)[CH2:37]2)=[O:41])=[CH:46][CH:45]=1

Participants

4

Reactant 1

HCID 59410177HCID 59410177, compound

Product 1

HCID 251438335-Chloro-N-{[(5S)-3-{4-[3-(2-hydroxyethyl)-2-oxopyridin-1(2H)-yl]-3-methoxyphenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

At 0° C., 37 g (49 mmol) of the compound from Example 24A are dissolved in 313 ml of 1.25N hydrochloric acid in methanol. After 1 h, the solution is evaporated under reduced pressure and diluted with dichloromethane. The organic phase is washed twice with water, dried over magnesium sulphate and, after filtration, evaporated to dryness under reduced pressure. The residue is chromatographed on silica gel using a gradient of dichloromethane and methanol. The product fractions are combined and evaporated to dryness under reduced pressure. This gives 19 g (78% of theory) of the desired product.

Workup

  1. customthe solution is evaporated under reduced pressure
  2. additiondiluted with dichloromethane
  3. washThe organic phase is washed twice with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationafter filtration
  6. customevaporated to dryness under reduced pressure
  7. customThe residue is chromatographed on silica gel using a gradient of dichloromethane and methanol
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-dae0213cb0a6448caefdc9d4d07e029a
Source dataset
uspto-grants-2013_02
Patent number
US08383822B2

Reaction notes

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