Sodium Azide → HCID 86606017, compound

HRID 658527Notes

Reaction equation

HRID 658527 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:7][C:8]([C@:10]1([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@@H:15](OS(C(F)(F)F)(=O)=O)[CH2:14][C@@H:13]2[C@H:11]1[C@@:12]2([F:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:9])[CH3:6]>CN(C)C=O.C(OCC)C>[CH2:5]([O:7][C:8]([C@:10]1([NH:30][C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[C@H:15]([N:1]=[N+:2]=[N-:3])[CH2:14][C@@H:13]2[C@H:11]1[C@@:12]2([F:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:9])[CH3:6]

Participants

5

Reactant 2

HCID 33557Sodium Azide2×HCID 86606018HCID 86606018, compound

Product 1

HCID 86606017HCID 86606017, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

313 mg of sodium azide was added to 1.63 g of (1R, 2R, 3S, 5R, 6R)-2-t-butoxycarbonylamino-6-fluoro-3-trifluoromethanesulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 16.3 mL of N,N-dimethylformamide, and the mixture was stirred for 1 hour at room temperature, and then for 20 hours at 35° C. 104 mg of sodium azide was further added thereto, and the mixture was stirred for 18 hours at 35° C. After being diluted with 50 mL of diethyl ether, the mixture was washed twice with water and then with a saturated aqueous solution of sodium chloride. The organic layers were dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200, eluent: hexane-ethyl acetate=5:1), thereby yielding 775 mg of (1R, 2R, 3R, 5R, 6R)-3-azido-2-t-butoxycarbonylamino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

Workup

  1. waitfor 20 hours at 35° C
  2. stirringthe mixture was stirred for 18 hours at 35° C
  3. washthe mixture was washed twice with water
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel: Wako gel C200, eluent: hexane-ethyl acetate=5:1)

Sources & evidence

ORD record
ord-aced0bcecc66453398dc8336d4561668
Source dataset
uspto-grants-2011_12
Patent number
US08076502B2

Reaction notes

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