Potassium Sodium Tartrate → HCID 69335514, compound

HRID 1295363Notes

Reaction equation

HRID 1295363 reaction equation
C([Mg]Cl)(C)C.CO[C:8](=[O:27])[C@@H:9]([N:16]([CH2:24][CH:25]=[CH2:26])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C(=O)(O)[O-].[Na+]>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CCOC(C)=O>[CH2:17]([N:16]1[CH2:24][CH:25]2[C@:8]([OH:27])([CH2:26]2)[C@@H:9]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 516892Sodium BicarbonateHCID 58907344HCID 58907344, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 69335514HCID 69335514, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

To a flame dried, 3 neck rbf equipped with an addition funnel was added THF (20 mL) and titanium(IV) isopropoxide (2.6 mL, 8.8 mmol) and the flask immersed in a −78° C. bath. To this mixture was added isopropylmagnesium chloride (2M/diethyl ether, 8.8 mL, 17.6 mmol) dropwise and stirring continued at −78° C. for 15 minutes. To the reaction flask was then added the starting material (S)-(allyl-benzyl-amino)-phenyl-acetic acid methyl ester (JACS, 19, 30, 1997, 6984) (˜40% pure, 2.0 g, 2.7 mmol dropwise in THF (7 mL total) and the reaction was allowed to stir at −78° C. for 2.5 hours, warmed to −10° C., stirred for an additional 3 hours, allowed to warm to room temperature gradually and stirred for 16 hours. The reaction was poured carefully into a saturated Rochelle's Salt solution, solid sodium bicarbonate was added until the pH=8, EtOAc was added and the mixture allowed to stir for 1 hour. The phases were separated and the aqueous extracted with ETOAc, the combined organics were washed with brine and dried over calcium sulfate, filtered and concentrated. The crude product was purified on a Biotage flash 40 system eluted with a gradient of Hexanes to 12% ETOAc/Hexanes to give the title compound as an oil. (0.57 g, 32% yield).

Workup

  1. customTo a flame dried
  2. custom3 neck rbf equipped with an addition funnel
  3. customimmersed in a −78° C.
  4. stirringto stir at −78° C. for 2.5 hours
  5. stirringstirred for an additional 3 hours
  6. temperatureto warm to room temperature gradually
  7. stirringstirred for 16 hours
  8. additionwas added
  9. stirringto stir for 1 hour
  10. customThe phases were separated
  11. extractionthe aqueous extracted with ETOAc
  12. washthe combined organics were washed with brine
  13. dry with materialdried over calcium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customThe crude product was purified on a Biotage flash 40 system
  17. washeluted with a gradient of Hexanes to 12% ETOAc/Hexanes

Sources & evidence

ORD record
ord-b996229d50874336b909ba11d4ace6f7
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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