Dicyclohexylcarbodiimide → HCID 15057637, compound

HRID 654026Notes

Reaction equation

HRID 654026 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]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](O)=[O:18])(=[O:13])=[O:12].OC1C2N=NNC=2C=CC=1.[OH:33][CH:34]([CH:37]1[CH2:41][O:40][C:39]([CH3:43])([CH3:42])[O:38]1)[CH2:35][NH2:36].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[OH:33][CH:34]([CH:37]1[CH2:41][O:40][C:39]([CH3:43])([CH3:42])[O:38]1)[CH2:35][NH:36][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[C:14]([S:11](=[O:13])(=[O:12])[NH:10][C:3]2[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:15]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11971028alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanolHCID 15057636HCID 15057636, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 15057637HCID 15057637, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

5.96 g (18 mmol) of 3-[N-(2,4,6-trifluorophenyl)sulfamoyl]-benzoic acid is dissolved in 50 ml of dry dimethylformamide under argon atmosphere, 2.76 g (18 mmol) of hydroxybenzotriazole and 2.9 (18 mmol) of 2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamine are added and the solution is cooled to -10° C. At this temperature, 3.71 g (18 mmol) of dicyclohexylcarbodiimide is added to the solution. Then it is stirred for 1 hour at -10° C. and 6 hours at room temperature. The turbid reaction solution is filtered and the filtrate is concentrated by evaporation in a vacuum. The residue is dissolved in 100 ml of ethyl acetate, the solution is shaken out five times with saturated sodium bicarbonate solution and twice with water, the organic phase is dried on sodium sulfate, filtered and concentrated by evaporation. The residue is chromatographed on silica gel 60 (Merck) with ethyl acetate/hexane. 4.91 g (10.35 mmol)=57.5% of the theoretical yield is obtained as an amorphous solid.

Workup

  1. customThe turbid reaction solution
  2. filtrationis filtered
  3. concentrationthe filtrate is concentrated by evaporation 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 materialtwice with water, the organic phase is dried on sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe residue is chromatographed on silica gel 60 (Merck) with ethyl acetate/hexane
  10. custom4.91 g (10.35 mmol)=57.5% of the theoretical yield
  11. customis obtained as an amorphous solid

Sources & evidence

ORD record
ord-862f74937cb94db983076561833e83ff
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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