Dicyclohexylcarbodiimide → HCID 54710609, compound

HRID 634844Notes

Reaction equation

HRID 634844 reaction equation
[C:1]([C:4]1[O:8][C:7]([CH2:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH:13][C:14]1[CH:19]=[C:18]([CH3:20])[O:17][C:16](=[O:21])[CH:15]=1.C1CCC(N=C=NC2CCCCC2)CC1.[Na].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C.C(O)C>[C:1]([C:4]1[O:8][C:7]([CH2:9][C:10]([C:15]2[C:16](=[O:21])[O:17][C:18]([CH3:20])=[CH:19][C:14]=2[OH:13])=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

9

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 21260725HCID 21260725, compoundHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54710609HCID 54710609, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

The 2.49 g (14.8 mmol) of 5-acetyl-2-furanacetic acid, 1.87 g (14.8 mmol) of 4-hydroxy-6-methyl-2-pyrone and 3.37 g (16.3 mmol) of DCC were suspended in 25 ml of chloroform, then 183 mg (1.50 mmol) of DMAP added and stirring carried out overnight at 60° C. The reaction liquid was 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 ethanol and Compound 13 (496 mg, 1.79 mmol, 12%) obtained. This was converted to the sodium salt with an equivalent quantity 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. customobtained

Sources & evidence

ORD record
ord-7847e04511854d6dacb3322be982dd82
Source dataset
uspto-grants-2001_02
Patent number
US06184245B2

Reaction notes

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