Dicyclohexylcarbodiimide → HCID 54712964, compound

HRID 634843Notes

Reaction equation

HRID 634843 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[S:4][C:3]=1[CH2:8][C:9]([OH:11])=O.[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[O:16][C:15](=[O:20])[CH:14]=1.C1CCC(N=C=NC2CCCCC2)CC1.[Na].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.C(O)C>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[S:4][C:3]=1[CH2:8][C:9]([C:14]1[C:15](=[O:20])[O:16][C:17]([CH3:19])=[CH:18][C:13]=1[OH:12])=[O:11]

Participants

9

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 21260742222553-93-7HCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54712964HCID 54712964, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

The 3.82 g (22.4 mmol) of 3,5-dimethylthiopheneacetic acid, 2.87 g (22.7 mmol) of 4-hydroxy-6-methyl-2-pyrone and 5.13 g (24.8 mmol) of DCC were suspended in 70 ml of toluene, then 273 mg (2.23 mmol) of DMAP added and stirring carried out overnight at 90° 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 12 (684 mg, 2.45 mmol, 11%) 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-9c18844806ae4235805f5cacc03e9524
Source dataset
uspto-grants-2001_02
Patent number
US06184245B2

Reaction notes

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