Dimethylformamide → Methyl 3-[5-(1,2-dithiolan-3-yl)pentyl]ureidoacetate

HRID 849585Notes

Reaction equation

HRID 849585 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]C(O)=O)[S:2]1.Cl.[CH3:15][O:16][C:17](=[O:20])[CH2:18][NH2:19].C[N:22](C)[CH:23]=[O:24]>C1(C)C=CC=CC=1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:22][C:23](=[O:24])[NH:19][CH2:18][C:17]([O:16][CH3:15])=[O:20])[S:2]1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 122755Glycine methyl ester hydrochlorideHCID 226203646-(1,2-Dithiolan-3-yl)hexanoic acid

Product 1

HCID 18358079Methyl 3-[5-(1,2-dithiolan-3-yl)pentyl]ureidoacetate

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolventHCID 199401P,P-Diphenylphosphinic azideSolvent

Procedure

The reaction was carried out as described in Example 46, but using 10 ml of a solution of 1.5 mmol of 6-(1,2-dithiolan-3-yl)hexanoic acid (prepared as described in Example 104) in toluene, 6 ml of anhydrous toluene, 0.42 ml of triethylamine, 0.39 ml of diphenylphosphoryl azide, 6 ml of anhydrous dimethylformamide and 254 mg of glycine methyl ester hydrochloride. The solvent was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue, after which it was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 1:4 and 3:2 by volume mixtures of ethyl acetate and hexane as the eluent. The solvent was removed from the eluate by evaporation under reduced pressure, and the residue was dissolved in dioxane and then lyophilised, to obtain 16 mg of the title compound as yellow crystals having an Rf value of 0.62 (silica gel thin layer chromatography; using a 2:3 by volume mixture of ethyl acetate and hexane as developing solvent).

Workup

  1. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
  7. customThe solvent was removed from the
  8. customeluate by evaporation under reduced pressure
  9. dissolutionthe residue was dissolved in dioxane

Sources & evidence

ORD record
ord-972d59fa65104d8a8e4735c3e1b700fa
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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