Formic Acid → HCID 71471050, compound

HRID 927852Notes

Reaction equation

HRID 927852 reaction equation
[OH-].[Li+].[C:3]1([S:9]([NH:12][C:13]2[C:22]([C:23]([O:25]C)=[O:24])=[C:21]3[C:16]([C@H:17]4[CH2:29][CH2:28][O:27][C@H:18]4[CH2:19][O:20]3)=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)=O>O1CCOCC1.O>[C:3]1([S:9]([NH:12][C:13]2[C:22]([C:23]([OH:25])=[O:24])=[C:21]3[C:16]([C@H:17]4[CH2:29][CH2:28][O:27][C@H:18]4[CH2:19][O:20]3)=[CH:15][CH:14]=2)(=[O:10])=[O:11])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 3939Lithium Hydroxide2×HCID 86713239HCID 86713239, compound2×

Product 1

HCID 71471050HCID 71471050, compoundYield 24.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide (0.048 g) was added to a solution of methyl cis-(3aRS,9bRS)-7-(benzenesulfonylamino)-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylate (Intermediate 1, 0.08 g) in a mixture of dioxane (10 mL) and water (5 mL) and the resultant mixture was irradiated in the microwave at 110° C. with air cooling for 20 minutes. Further lithium hydroxide (0.2 g) was added and the mixture was irradiated in the microwave at 110° C. with air cooling for a total of 80 minutes. After cooling, the solution was acidified by addition of aqueous formic acid solution (10%) and the resultant mixture was extracted with ethyl acetate, dried (MgSO4) and filtered. The filtrate was evaporated to dryness. The residue was dissolved in a mixture of methanol (10 mL) and water (5 mL) and treated with lithium hydroxide (0.2 g) then irradiated in the microwave at 110° C. with air cooling for 40 minutes. After cooling, the solution was acidified by addition of formic acid (10%) and the resultant mixture was extracted with ethyl acetate, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by preparative HPLC (C18) eluting with a mixture of acetonitrile and water, containing 0.1% formic acid, with a gradient of 30-50% to give cis-(3aRS,9bRS)-7-(benzenesulfonylamino)-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylic acid (0.019 g) as a white solid.

Workup

  1. temperaturecooling for 20 minutes
  2. customthe mixture was irradiated in the microwave at 110° C. with air
  3. temperaturecooling for a total of 80 minutes
  4. temperatureAfter cooling
  5. extractionthe resultant mixture was extracted with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. dissolutionThe residue was dissolved in a mixture of methanol (10 mL) and water (5 mL)
  10. additiontreated with lithium hydroxide (0.2 g)
  11. customthen irradiated in the microwave at 110° C. with air
  12. temperaturecooling for 40 minutes
  13. temperatureAfter cooling
  14. additionthe solution was acidified by addition of formic acid (10%)
  15. extractionthe resultant mixture was extracted with ethyl acetate
  16. dry with materialdried (MgSO4)
  17. filtrationfiltered
  18. customThe filtrate was evaporated to dryness
  19. customthe residue was purified by preparative HPLC (C18)
  20. washeluting with a mixture of acetonitrile and water
  21. additioncontaining 0.1% formic acid

Sources & evidence

ORD record
ord-ca208d228f3046ccae30b684ee1fbfd9
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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