Sodium Bicarbonate → HCID 69911377, compound

HRID 353389Notes

Reaction equation

HRID 353389 reaction equation
C(=O)(O)[O-].[Na+:5].[C:6]([O:10][C:11](=[O:26])[CH2:12]/[C:13](=[CH:17]\[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)/[C:14]([OH:16])=[O:15])([CH3:9])([CH3:8])[CH3:7]>CO.O>[Na+:5].[C:6]([O:10][C:11](=[O:26])[CH2:12][C@@H:13]([CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]([O-:16])=[O:15])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 9835650(E)-2-[2-(tert-Butoxy)-2-oxoethyl]-5-phenyl-2-pentenoic acid

Product 1

HCID 69911377HCID 69911377, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
22.5 °C

Procedure

A stirred solution of sodium bicarbonate (28.6 g, 0.34 mol), (E)-2-[2-(tert-butoxy)-2-oxoethyl]-5-phenyl-2-pentenoic acid (100 g, 0.34 mol) and [(S)-2,2′-bis(diphenylphosphino-1,1′-binaphthyl]chloro(p-cymene)ruthenium chloride (0.63 g, 0.68 mmol) in methanol (750 ml) and water (250 ml) was heated to 60° C., under hydrogen (60 p.s.i.), for 24 hours and then allowed to cool to 20-25° C. (enantiomeric excess 87%). The mixture was filtered through a filter aid Celite® and the solvent was stripped and replaced with acetonitrile by distillation at atmospheric pressure, at a constant volume of 500 ml. The resulting suspension was cooled to 20-25° C. and was stirred for 24 hours, then filtered. The residue was washed with acetonitrile (3×25 ml) and then dried in vacuo at 45° C. for 3 hours to leave the title compound as a colourless solid (65 g, 61% yield, enantiomeric excess=94.3%, 95% pure by NMR).

Workup

  1. filtrationThe mixture was filtered through a filter aid Celite®
  2. distillationreplaced with acetonitrile by distillation at atmospheric pressure, at a constant volume of 500 ml
  3. temperatureThe resulting suspension was cooled to 20-25° C.
  4. filtrationfiltered
  5. washThe residue was washed with acetonitrile (3×25 ml)
  6. customdried in vacuo at 45° C. for 3 hours

Sources & evidence

ORD record
ord-c21939201f084aad95fcc8dfb7cf95f6
Source dataset
uspto-grants-2004_06
Patent number
US06750363B2

Reaction notes

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