Sodium Azide → HCID 86717550, compound

HRID 712098Notes

Reaction equation

HRID 712098 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][C@H:16](OS(C)(=O)=O)[CH2:15][CH2:14][C@@H:13]1[C:23]([O:25][CH3:26])=[O:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:27]=[N+:28]=[N-:29].[Na+].C([O-])(O)=O.[Na+].O>CN(C)C=O>[N:27]([C@H:16]1[CH2:15][CH2:14][C@H:13]([C:23]([O:25][CH3:26])=[O:24])[C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:17]1)=[N+:28]=[N-:29]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 86585896Sodium bicarbonate waterHCID 86717551HCID 86717551, compound

Product 1

HCID 86717550HCID 86717550, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl (1S,2R,4R)-2-{[(benzyloxy)carbonyl]amino}-4-[(methylsulfonyl)oxy]cyclohexanecarboxylate (0.30 g, 0.78 mmol) in N,N-dimethylformamide (2.6 mL) was added sodium azide (0.20 g, 3.1 mmol). The reaction was heated to 80° C. and stirred for 2.5 h. After cooling, the reaction mixture was poured into sat. NaHCO3/water and extracted with EtOAc (3 x). The combined extracts were washed with brine, dried (Na2SO4), and concentrated. The crude was purified on silica gel, eluting with 0-40% EtOAc in hexanes to give 187 mg (72%) of the desired product as a clear gum. LCMS calculated for C16H21N2O4 (M+H-28)+: m/z=305.2. Found: 305.1.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc (3 x)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude was purified on silica gel
  7. washeluting with 0-40% EtOAc in hexanes

Sources & evidence

ORD record
ord-c801f4a98f584b33b78f80be2c2bbcc7
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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