Dicyclohexylcarbodiimide → (1-propargyl-2,4-dioxo-imidazolidin-3-yl)-methyl(1R,trans)2,2-dimethyl-3-(cyclobutylidenemethyl)-cyclopropane-1-carboxylate

HRID 867893Notes

Reaction equation

HRID 867893 reaction equation
[CH2:1]([N:4]1[CH2:8][C:7](=[O:9])[N:6]([CH2:10][OH:11])[C:5]1=[O:12])[C:2]#[CH:3].[CH3:13][C:14]1([CH3:25])[C@H:16]([CH:17]=[C:18]2[CH2:21][CH2:20][CH2:19]2)[C@H:15]1[C:22](O)=[O:23].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:13][C:14]1([CH3:25])[C@H:16]([CH:17]=[C:18]2[CH2:19][CH2:20][CH2:21]2)[C@H:15]1[C:22]([O:11][CH2:10][N:6]1[C:7](=[O:9])[CH2:8][N:4]([CH2:1][C:2]#[CH:3])[C:5]1=[O:12])=[O:23]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 117895972,4-Imidazolidinedione, 3-(hydroxymethyl)-1-(2-propynyl)-HCID 13241313(1R,trans) 2,2-dimethyl-3-cyclobutylidenemethyl-cyclopropane-1-carboxylic acid

Product 1

HCID 13241316(1-propargyl-2,4-dioxo-imidazolidin-3-yl)-methyl(1R,trans)2,2-dimethyl-3-(cyclobutylidenemethyl)-cyclopropane-1-carboxylateYield 17%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.6 g of (1-propargyl-2,4-dioxo-imidazolidin-3-yl)-methanol in 10 ml of methylene chloride was added at 20° C. to a mixture of 4 g of (1R,trans)2,2-dimethyl-3-(cyclobutylidenemethyl)-cyclopropane-1-carboxylic acid, 4.6 g of dicyclohexylcarbodiimide, 20 ml of methylene chloride and a catalytic amount of 4-dimethylamino-pyridine and the mixture was stirred at 20° C. for 17 hours and was vacuum filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 7-3 cyclohexane-ethyl actate mixture and then a 95-5 benzene-ethyl acetate mixture yielded 1.2 g of (1-propargyl-2,4-dioxo-imidazolidin-3-yl)-methyl(1R,trans)2,2-dimethyl-3-(cyclobutylidenemethyl)-cyclopropane-1-carboxylate.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. customthe residue was chromatographed over silica gel
  4. washElution with a 7-3 cyclohexane-ethyl actate mixture

Sources & evidence

ORD record
ord-8e733ca2a2584a49af4fd529ac060fc7
Source dataset
uspto-grants-1988_10
Patent number
US04777180

Reaction notes

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