Dicyclohexylcarbodiimide → HCID 19602479, compound

HRID 1604253Notes

Reaction equation

HRID 1604253 reaction equation
[N:1]([CH2:4][CH:5]1[O:11][CH:10]2[N:7]([C:8](=[O:12])[CH2:9]2)[CH2:6]1)=[N+]=[N-].[C:13](O)(=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17].C1(N=C=NC2CCCCC2)CCCCC1>[Pd].C(OCC)(=O)C>[C:13]([NH:1][CH2:4][CH:5]1[O:11][CH:10]2[N:7]([C:8](=[O:12])[CH2:9]2)[CH2:6]1)(=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 611384-Pentenoic acidHCID 19602468HCID 19602468, compound

Product 1

HCID 19602479HCID 19602479, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

600 mg of (3RS,5RS)-3-Azidomethyl-4-oxa-1-azabicyclo[3.2.0]heptan-7-one was hydrogenated with 1.0 g of 10% Palladium on activated carbon in Ethyl acetate at 50 psi for 1 hr. After removal of catalyst by filtration, 360 mg (3.6 mmol) of 4-Pentenoic acid and 300 mg (1.8 mmol) of 1,3-Dicyclohexyl carbodiimide were added under ice-cooling. The reaction mixture was then stirred at room temperature for 2 hrs. Resulted solid was filtered off and the filtrate was concentrated in vacuo. The residue was purified by flash silicagel column using Hexane-Ethyl acetate (1:1) as eluent and the title compound was obtained as oil.

Workup

  1. customAfter removal of catalyst
  2. additionwere added under ice-
  3. temperaturecooling
  4. customResulted solid
  5. filtrationwas filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by flash silicagel column

Sources & evidence

ORD record
ord-8a7f7594ff074ddea4803daac488ecc4
Source dataset
uspto-grants-1999_11
Patent number
US05994342

Reaction notes

Loading…