Benzoate → HCID 18640477, compound

HRID 2166486Notes

Reaction equation

HRID 2166486 reaction equation
C1COCC1.C([O-])(=O)C1C=CC=CC=1.[Li+].[OH-].[OH:17][CH2:18][C@H:19]1[O:23][C:22](=[O:24])[N:21]([CH:25]([CH3:27])[CH3:26])[C@@H:20]1[CH3:28]>O>[OH:17][CH2:18][C@H:19]1[O:23][C:22](=[O:24])[N:21]([CH:25]([CH3:27])[CH3:26])[C@H:20]1[CH3:28]

Participants

6

Reactant 4

HCID 242BenzoateHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 18640470HCID 18640470, compound

Product 1

HCID 18640477HCID 18640477, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A THF (87 ml) solution of 4.80 grams of (S)(S)-oxazolidinone from Step G was stirred at 22° C. and treated with 87 ml of 1N LiOH in H2O. After 2.5 hours at 22° C. the THF was removed by rotary evaporation and the product extracted with CH2Cl2. The combined organic portions were washed with saturated aqueous Na2CO3, H2O, and brine, dried (Na2SO4) and concentrated to essentially pure product as a white foam; yield 2.93 g (95%). ##STR25## Similarly prepared is the 5(S)-hydroxymethyl-4(R)-methyl-3-(1-methylethyl)oxazolidin-2-one.

Workup

  1. customAfter 2.5 hours at 22° C. the THF was removed by rotary evaporation
  2. extractionthe product extracted with CH2Cl2
  3. washThe combined organic portions were washed with saturated aqueous Na2CO3, H2O, and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to essentially pure product as a white foam
  6. custom##STR25## Similarly prepared

Sources & evidence

ORD record
ord-1dcf2e122877475281306978ed932706
Source dataset
uspto-grants-1990_07
Patent number
US04945182

Reaction notes

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