Hydrochloric Acid → HCID 54462173, compound

HRID 374511Notes

Reaction equation

HRID 374511 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][CH:17]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29](OC)=[O:30])=[CH:23][CH:22]=3)[O:16][C:15]2=[O:33])=[CH:10][CH:9]=1.Cl>O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:18][CH:17]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][OH:30])=[CH:23][CH:22]=3)[O:16][C:15]2=[O:33])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18997185HCID 18997185, compound2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 54462173HCID 54462173, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (59 mg) was added to a tetrahydrofuran (15 ml) solution of 750 mg of methyl 3-{4-[3-(4-chlorophenyl)-2-oxooxazolidin-5-yl]methoxy-phenyl}propionate (compound 191) obtained in Example 32. The mixture was stirred with ice-cooling for 40 minutes in a stream of nitrogen. To the reaction mixture was added 5% hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and purified by hexane-ethyl acetate gradient elution to give 498 mg of the title compound (compound 194) in a yield of 71%.

Workup

  1. customobtained in Example 32
  2. temperaturecooling for 40 minutes in a stream of nitrogen
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. custompurified by hexane-ethyl acetate gradient elution

Sources & evidence

ORD record
ord-2432d91e89664c569f715fd873d58f0e
Source dataset
uspto-grants-1996_01
Patent number
US05480899

Reaction notes

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