Hydrochloric Acid → HCID 24963431, compound

HRID 1160482Notes

Reaction equation

HRID 1160482 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:28])[C@@H:15]([O:24][CH:25]([CH3:27])[CH3:26])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=1)C1C=CC=CC=1.[OH-].[Li+].Cl.S([O-])([O-])=[O:33].[Na+].[Na+]>O1CCCC1.OO>[OH:23][C:19]1[CH:18]=[C:17]([CH2:16][C@H:15]([O:24][CH:25]([CH3:26])[CH3:27])[C:14]([OH:28])=[O:33])[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 57719497HCID 57719497, compound

Product 1

HCID 24963431HCID 24963431, compound

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

129.9 g of (4S)-4-benzyl-3-[(2S)-3-(3-hydroxyphenyl)-2-isopropoxypropionyl]-1,3-oxazolidin-2-one was dissolved in 2 L of tetrahydrofuran, to which 140 mL of 30% hydrogen peroxide solution was added. Under cooling with ice, 700 mL of 1N lithium hydroxide solution was added dropwise, followed by stirring at 0° C. for 1 hour. To the reaction mixture was added 1N hydrochloric acid (500 mL), to which a sodium sulfite aqueous solution (10%, 500 mL) was then added slowly. The mixture was poured into a separating funnel to separate a tetrahydrofuran layer, followed by making the aqueous layer at pH 2 with 1N hydrochloric acid before extraction 3 times with ethyl acetate (1 L). The organic layers were combined and washed with a saturated sodium chloride solution (1.5 L) before drying the organic layer with anhydrous magnesium sulfate, followed by distilling off the solvent under a reduced pressure to obtain 130 g of (2S)-3-(3-hydroxyphenyl)-2-isopropoxypropionic acid. This compound was dissolved in 1 L of N,N-dimethylformamide, to which 67.8 g of potassium bicarbonate and 100 mL of ethyl iodide were sequentially added under cooling with ice, followed by stirring the reaction mixture at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and washed sequentially with 1N hydrochloric acid and a saturated sodium chloride solution. The organic layer was dried with anhydrous magnesium sulfate, followed by distilling off the solvent under a reduced pressure. The residue was purified using silica gel column chromatography to obtain 61.8 g of the title compound in the form of colorless oily matter from a hexane-ethyl acetate (3:1)-eluted fraction.

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. additionThe mixture was poured into a separating funnel
  4. customto separate a tetrahydrofuran layer
  5. extractionbefore extraction 3 times with ethyl acetate (1 L)
  6. washwashed with a saturated sodium chloride solution (1.5 L)
  7. dry with materialbefore drying the organic layer with anhydrous magnesium sulfate
  8. distillationby distilling off the solvent under a reduced pressure

Sources & evidence

ORD record
ord-eddcf1938e5d4c00b3360fab2558e505
Source dataset
uspto-grants-2010_10
Patent number
US07816405B2

Reaction notes

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