tert-Butanol → HCID 178453943, compound

HRID 1398077Notes

Reaction equation

HRID 1398077 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6](C(O)=O)[CH2:5][CH2:4]1)#[N:2].C([N:14]([CH2:17]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C(OCC)(=O)C.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:1]([C@H:3]1[CH2:4][CH2:5][C@H:6]([NH:14][C:17](=[O:26])[O:46][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:7][CH2:8]1)#[N:2]

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 178511260HCID 178511260, compound

Product 1

HCID 178453943HCID 178453943, compoundYield 54%

Procedure

To a solution of 765 mg (4.99 mmol) of trans-4-cyanocyclohexane carboxylic acid in 10 mL of tert-butanol was added 766 μL (5.49 mmol) of triethylamine and 1.13 mL (5.24 mmol) of diphenylphosphorylazide at room temperature, and the mixture was refluxed for 6 hours. After the reaction mixture was cooled to room temperature, ethyl acetate was added to this mixture and the organic layer was washed with saturated sodium bicarbonate aqueous solution, then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to give 608 mg (54%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. washthe organic layer was washed with saturated sodium bicarbonate aqueous solution
  3. dry with materialdried over with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-17b6c2c36cd74a07a453b7226bf42405
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

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