Sodium Azide → HCID 76528971, compound

HRID 56425Notes

Reaction equation

HRID 56425 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH:14](OS(C)(=O)=O)[CH2:13][CH2:12][CH:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+]>CS(C)=O.C(OCC)(=O)C>[N:25]([CH:14]1[CH2:13][CH2:12][CH:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:10][CH:9]1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N+:26]=[N-:27]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 87507560C15H27NO7S

Product 1

HCID 76528971HCID 76528971, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of Racemate-ethyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)cyclohexanecarboxylate (11.0 g, 30 mmol) in dimethyl sulfoxide (110 mL) was added sodium azide (20 g, 300 mmol), and the mixture was stirred at 90° C. overnight under N2. The solution was cooled to ˜30° C., dissolved in ethyl acetate (˜500 mL), washed with water (500 mL×5) and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=4:1˜2:1) to thereby give the title compound (4.1 g, 44%) as an colorless oil. MS (ES+) C14H24N4O4 requires: 312, found: 213 [M+H−100]+.

Workup

  1. temperatureThe solution was cooled to ˜30° C.
  2. washwashed with water (500 mL×5) and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=4:1˜2:1)

Sources & evidence

ORD record
ord-92c1b9af0b7b466cac1c75e62fe3fab5
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

Loading…