Sodium Bicarbonate → HCID 11020266, compound

HRID 381786Notes

Reaction equation

HRID 381786 reaction equation
[Cl:1][C@@H:2]([C@H:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[C:14](=O)(O)[O-].[Na+]>CO>[Cl:1][C@@H:2]([C@H:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:14])=[O:4]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 11458316HCID 11458316, compound

Product 1

HCID 11020266HCID 11020266, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2S,3R)-2-chloro-3-hydroxy-3-phenyl propionic acid (CIV, EXAMPLE 3, 2 g, 10 mmol) in methanol (20 ml, saturated with hydrochloric acid) is stirred at 25° for 1 hr. The reaction mixture is poured into a saturated aqueous sodium bicarbonate (20 ml) and extracted with ethyl acetate (20 ml×3). The combined organic phases are washed with water (20 ml) and dried over magnesium sulfate. Filtration and solvent removal under reduced pressure gives the title compound, [α]25D=−5.0° (c=1.5, CHCl3); NMR (300 MHz, CDCl3) 7.41-7.35, 5.19, 4.51 and 3.70 δ; CMR (300 MHz, CDCl3) 168.4, 138.1, 128.7, 128.5, 126.5, 74.4, 62.8 and 53.0 δ.

Workup

  1. extractionextracted with ethyl acetate (20 ml×3)
  2. washThe combined organic phases are washed with water (20 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and solvent removal under reduced pressure

Sources & evidence

ORD record
ord-3df4bc34f9434897bdf196797efbf8e6
Source dataset
uspto-grants-2001_10
Patent number
US06307064B1

Reaction notes

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