Dimethyl Sulfoxide → HCID 59569815, compound

HRID 2071142Notes

Reaction equation

HRID 2071142 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([C:24]([O:26][CH3:27])=[O:25])[CH:17]=[C:18]([CH:23]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:10]1.N1C=CC=CC=1.CS(C)=O.C1(N=C=NC2CCCCC2)CCCCC1>C1C=CC=CC=1.CCOCC.O>[O:8]=[C:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[CH:17]=[C:16]([CH:15]=2)[C:24]([O:26][CH3:27])=[O:25])[CH2:10]1

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 59569771HCID 59569771, compound

Product 1

HCID 59569815HCID 59569815, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 21584184Diethylether waterSolvent

Procedure

Trifluoroacetic acid (0.061 ml, 0.091 g, 0.794 mmol, 0.5 eq) was added dropwise to a stirred solution of dimethyl 5-(3-hydroxypyrrolidin-1-yl)isophthalate (0.4434 g, 1.59 mmol, 1 eq), anhydrous pyridine (0.135 ml, 0.13 g, 1.67 mmol, 1.05 eq), anhydrous DMSO (0.124 ml, 0.13 g, 1.67 mmol, 1.05 eq), and 1,3-dicyclohexylcarbodiimide (0.655 g, 3.18 mmol, 2 eq) in 5 ml anhydrous benzene at ° C. under Ar. After stirring at 0° C. to room temperature overnight the reaction was diluted with Et2O/H2O and stirred for 20 h. The mixture was filtered through cotton and the layers were separated. The organic layer was washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off and the solvent was removed in vacuo. Purification via flash chromatography yielded only crude product. Purification via a second column yielded 0.201 g (0.73 mmol, 46% yield) of dimethyl 5-(3-oxopyrrolidin-1-yl)isophthalate.

Workup

  1. stirringstirred for 20 h
  2. filtrationThe mixture was filtered through cotton
  3. customthe layers were separated
  4. washThe organic layer was washed with water (×3), brine (×1)
  5. dry with materialdried over Na2SO4
  6. filtrationThe inorganics were filtered off
  7. customthe solvent was removed in vacuo
  8. customPurification via flash chromatography
  9. customyielded only crude product
  10. customPurification via a second column

Sources & evidence

ORD record
ord-98d2148843df4d7aad845423c9262846
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…