Dicyclohexylcarbodiimide → HCID 54712962, compound

HRID 634841Notes

Reaction equation

HRID 634841 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=O.[OH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:14][C:13](=[O:21])[CH:12]=1.C1CCC(N=C=NC2CCCCC2)CC1.[Na].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([C:12]1[C:13](=[O:21])[O:14][C:15]2[C:20]([C:11]=1[OH:10])=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:9]

Participants

8

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 75974Furan-2-acetic acidHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 546829304-Hydroxycoumarin

Product 1

HCID 54712962HCID 54712962, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

1.55 g (12.3 mmol) of the furanacetic acid, 1.99 g (12.3 mmol) of 4-hydroxycoumarin and 2.83 g (13.7 mmol) of DCC were suspended in 50 ml of toluene, then 149 mg (1.22 mmol) of DMAP added and stirring carried out overnight at 60° C. The reaction liquid was then cooled to room temperature and the insoluble material filtered off. The mother liquor was concentrated and the residue purified by column chromatography. The solid obtained was recrystallized from methanol and Compound 9. (594 mg, 2.20 mmol, 18%) obtained. This was converted to the sodium salt with an equivalent amount of sodium hydrogen carbonate.

Workup

  1. customThe reaction liquid
  2. filtrationthe insoluble material filtered off
  3. concentrationThe mother liquor was concentrated
  4. customthe residue purified by column chromatography
  5. customThe solid obtained
  6. customwas recrystallized from methanol and Compound 9
  7. custom(594 mg, 2.20 mmol, 18%) obtained

Sources & evidence

ORD record
ord-2e4fe98286cc43218d118af1124b1690
Source dataset
uspto-grants-2001_02
Patent number
US06184245B2

Reaction notes

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