Sodium Azide → HCID 178418853, compound

HRID 2225213Notes

Reaction equation

HRID 2225213 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12](OS(C)(=O)=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:20]=[N+:21]=[N-:22].[Na+]>CS(C)=O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([N:20]=[N+:21]=[N-:22])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 178418975HCID 178418975, compound

Product 1

HCID 178418853HCID 178418853, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of methanesulfonic acid trans-4-tert-butoxycarbonylamino-cyclohexyl ester (21 g, 72 mmol) in DMSO (350 mL) was charged with sodium azide (14 g, 216 mmol) and heated at 65° C. for 14 h. After cooling to RT, the solution was diluted with EtOAc and washed successively with water, 5% aq. NaHCO3, water, and brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo, and the resulting residue was purified via flash chromatography to afford (cis-4-azido-cyclohexyl)-carbamic acid tert-butyl ester (16 g, 92% yield). MS found: (M+H)+=241.7.

Workup

  1. temperatureAfter cooling to RT
  2. washwashed successively with water, 5% aq. NaHCO3, water, and brine
  3. dry with materialThe solution was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customthe resulting residue was purified via flash chromatography

Sources & evidence

ORD record
ord-a4cb46ae9ae341e3ba7e4d7d1d20b097
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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