Dicyclohexylcarbodiimide → 2-[N-(2,4,6-Trifluorophenyl)sulfamoyl]-acetic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide]

HRID 654008Notes

Reaction equation

HRID 654008 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[NH:10][S:11]([CH2:14][C:15]([OH:17])=O)(=[O:13])=[O:12].[OH:18][CH:19]([CH:22]1[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]1)[CH2:20][NH2:21].OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[OH:18][CH:19]([CH:22]1[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]1)[CH2:20][NH:21][C:15](=[O:17])[CH2:14][S:11](=[O:12])(=[O:13])[NH:10][C:3]1[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11971028alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanolHCID 150576012-[N-(2,4,6-trifluorophenyl)sulfamoyl] acetic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 150576032-[N-(2,4,6-Trifluorophenyl)sulfamoyl]-acetic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide]

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

1.38 g (3.16 mmol) of 2-[N-(2,4,6-trifluorophenyl)sulfamoyl] acetic acid is dissolved in 20 ml of DMF with exclusion of moisture and under argon atmosphere, 509 mg (3.16 mmol) of 2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamine and 484 mg (3.16 mmol) of hydroxybenzotriazole are added and the solution is cooled to -10° C. 652 mg (3.16 mmol) of dicyclohexylcarbodiimide is added to the cooled solution, it is stirred for one hour at -10° C and for 12 more hours at room temperature. The turbid reaction solution is then filtered and the clear filtrate is evaporated to dryness in a vacuum. The residue is dissolved in 100 ml of ethyl acetate and the solution is shaken out five times with saturated sodium bicarbonate solution and twice with water. The ethyl acetate solution is dried on sodium sulfate, filtered and evaporated to dryness. The residue is chromatographed on silica gel 60 (Merck) with ethyl acetate/methylene chloride 8:2. The corresponding fractions together contain 0.62 g (1.42 mmol)=45% of the theoretical yield of product is obtained as an amorphous solid.

Workup

  1. customThe turbid reaction solution
  2. filtrationis then filtered
  3. customthe clear filtrate is evaporated to dryness in a vacuum
  4. dissolutionThe residue is dissolved in 100 ml of ethyl acetate
  5. stirringthe solution is shaken out five times with saturated sodium bicarbonate solution
  6. dry with materialThe ethyl acetate solution is dried on sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue is chromatographed on silica gel 60 (Merck) with ethyl acetate/methylene chloride 8:2
  10. customThe corresponding fractions together contain 0.62 g (1.42 mmol)=45% of the theoretical yield of product is obtained as an amorphous solid

Sources & evidence

ORD record
ord-1e95eb18d4f54856821b5da2abe45231
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

Loading…