Water → HCID 86601560, compound

HRID 458294Notes

Reaction equation

HRID 458294 reaction equation
[C:1]1([CH3:42])[C:2]([S:7]([O:10][CH2:11][C@H:12]([CH2:21][O:22][C:23](=[O:41])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:13][CH:14](OCC)[O:15]CC)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.O.FC(F)(F)C(O)=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(OCC)(=O)C>[C:23]([O:22][CH2:21][C@@H:12]([CH2:11][O:10][S:7]([C:2]1[C:1]([CH3:42])=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:9])=[O:8])[CH2:13][CH:14]=[O:15])(=[O:41])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 86601559HCID 86601559, compound

Product 1

HCID 86601560HCID 86601560, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 31, step b) (29.38 g, assayed at 23.12 g, 0.037 moles) was dissolved in THF (90 mL) and charged into a 250 mL round bottomed flask equipped with a magnetic stir bar and a temperature probe. Charged water (38 mL) and cooled to 10° C. Trifluoroacetic acid (55 mL) was poured in and the mixture was stirred for 25 minutes. The reaction mixture was poured into a 2 L separatory funnel containing 20% (w/w) K2CO3 solution (690 g), ice (600 g), and ethyl acetate (500 mL). The upper organic layer was separated. The aqueous layer was extracted a second time with ethyl acetate (500 mL). The combined organic extracts were washed with 23% (w/w) NaCl solution. The organic layer was separated, dried with Na2SO4 and filtered. The solution was concentrated to 21.5 g of an oil, dissolved in heptane (150 mL), and stirred slowly (crystals formed after 10 minutes). The slurry was stirred 15 hrs. at ambient temperature, filtered and washed with ambient heptane (20 mL). The desired product was obtained as white crystals which were dried to a constant weight of 12.3 g.

Workup

  1. additioncharged into a 250 mL round bottomed flask
  2. customequipped with a magnetic stir bar
  3. additionThe reaction mixture was poured into a 2 L separatory funnel
  4. customThe upper organic layer was separated
  5. extractionThe aqueous layer was extracted a second time with ethyl acetate (500 mL)
  6. washThe combined organic extracts were washed with 23% (w/w) NaCl solution
  7. customThe organic layer was separated
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationThe solution was concentrated to 21.5 g of an oil
  11. dissolutiondissolved in heptane (150 mL)
  12. stirringstirred slowly
  13. custom(crystals formed after 10 minutes)
  14. stirringThe slurry was stirred 15 hrs
  15. filtrationat ambient temperature, filtered
  16. washwashed with ambient heptane (20 mL)

Sources & evidence

ORD record
ord-31d1ce8d717545a682c21825bf04c8d0
Source dataset
uspto-grants-2007_03
Patent number
US07189849B2

Reaction notes

Loading…