Dicyclohexylcarbodiimide → HCID 15057633, compound

HRID 654023Notes

Reaction equation

HRID 654023 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:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)(=[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:18](=[O:19])[C:17]1[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][CH:16]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11971028alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanolHCID 15057632HCID 15057632, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 15057633HCID 15057633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

4.97 g (15 mmol) of 4-[N-(2,4,6-trifluorophenyl)sulfamoyl]-benzoic acid is dissolved in 50 ml of dry dimethylformamide under argon atmosphere, 2.03 g (15 mmol) of hydroxybenzotriazole and 2.42 g (15 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, 3.09 g (15 mmol) of dicyclohexylcarbodiimide is added to the solution. Then it is stirred for 1 hour at -10° C. and 10 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. 3.46 g (7.29 mmol)=48.6% of the theoretical yield is obtained as a 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. custom3.46 g (7.29 mmol)=48.6% of the theoretical yield
  10. customis obtained as a solid

Sources & evidence

ORD record
ord-e574bb2ce47e49e08e7146d876618511
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

Loading…