Sodium Hydroxide → HCID 22861437, compound

HRID 374487Notes

Reaction equation

HRID 374487 reaction equation
[OH-].[Na+].[N+](C1C=CC(C([O:12][CH2:13][C@H:14]2[O:18][C:17](=[O:19])[N:16]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C@H:15]2[CH3:28])=O)=CC=1)([O-])=O>CO>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([N:16]2[C@@H:15]([CH3:28])[C@@H:14]([CH2:13][OH:12])[O:18][C:17]2=[O:19])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57080354HCID 57080354, compound

Product 1

HCID 22861437HCID 22861437, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A 3.8 ml quantity of 8% sodium hydroxide aqueous solution was added to a methanol (20 ml) solution of 2.43 g of (4S, 5S)-(-)-3-(4-methoxyphenyl)-4-methyl-2-oxooxazolidin-5-ylmethyl p-nitrobenzoate obtained in Reference Example 8. The mixture was stirred at 50° C. for 20 minutes. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with ethyl acetate. The extract was washed with water, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography and purified by hexane-ethyl acetate gradient elution to give 1.04 g of the title compound (yield 70%).

Workup

  1. customobtained in Reference Example 8
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionthe obtained residue was extracted with ethyl acetate
  4. washThe extract was washed with water
  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-3e087a2b7713431886b4474331788f6b
Source dataset
uspto-grants-1996_01
Patent number
US05480899

Reaction notes

Loading…