Water → HCID 57804674, compound

HRID 2360999Notes

Reaction equation

HRID 2360999 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].C([N+]1C=CC=CC=1)CCCCCCCCCCC.[C:24]([O:28][C:29]([NH:31][C@@H:32]1[CH2:37][C@@H:36]([C:38]([N:40]([CH3:42])[CH3:41])=[O:39])[CH2:35][CH2:34][C@H:33]1CS([O-])(=O)=O)=[O:30])([CH3:27])([CH3:26])[CH3:25].O>CN(C)C(=O)C.C(OCC)(=O)C>[C:24]([O:28][C:29](=[O:30])[NH:31][C@@H:32]1[CH2:37][C@@H:36]([C:38]([N:40]([CH3:41])[CH3:42])=[O:39])[CH2:35][CH2:34][C@H:33]1[N:1]=[N+:2]=[N-:3])([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 962WaterHCID 7717Dodecylpyridinium chlorideHCID 33557Sodium AzideHCID 131731286HCID 131731286, compound

Product 1

HCID 57804674HCID 57804674, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium azide (7.14 g) and dodecylpyridinium chloride (7.80 g) were added at room temperature to a solution (40 mL) of (1R,2R,4S)-2-[(t-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylmethanesulfonate (20.0 g) in N,N-dimethylacetamide (DMAC), followed by stirring at 60° C. for 72 hours. Water and ethyl acetate were added to the reaction mixture, and the organic layer was washed with aqueous saturated sodium bicarbonate solution and water. The solvent was evaporated under reduced pressure, and a solvent mixture (300 mL) of n-hexane and ethyl acetate (5:1) was added to the residue. The mixture was stirred at room temperature for 1 hour, and the formed crystals were recovered by filtration. A solvent mixture (300 mL) of n-hexane and ethyl acetate (5:1) was added to the recovered crystals, followed by stirring/recovering by filtration twice, to thereby yield 4.6 g of the title compound.

Workup

  1. washthe organic layer was washed with aqueous saturated sodium bicarbonate solution and water
  2. customThe solvent was evaporated under reduced pressure
  3. additiona solvent mixture (300 mL) of n-hexane and ethyl acetate (5:1) was added to the residue
  4. stirringThe mixture was stirred at room temperature for 1 hour
  5. filtrationthe formed crystals were recovered by filtration
  6. additionA solvent mixture (300 mL) of n-hexane and ethyl acetate (5:1) was added to the recovered crystals
  7. filtrationby stirring/recovering by filtration twice

Sources & evidence

ORD record
ord-3bccfdbfa8cc4925b3ae29d80341de39
Source dataset
uspto-grants-2014_04
Patent number
US08686189B2

Reaction notes

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