Dimethylformamide → HCID 58246862, compound

HRID 2355331Notes

Reaction equation

HRID 2355331 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C@H:9](OS(C)(=O)=O)[CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C=O)C.[N-:29]=[N+:30]=[N-:31].[Na+]>CCOC(C)=O.O>[N:29]([C@@H:9]([CH3:10])[C@@H:8]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[N+:30]=[N-:31]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 58246723HCID 58246723, compound

Product 1

HCID 58246862HCID 58246862, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl (2S,3R)-1-cyclohexyl-3-(methanesulfonyloxy)butan-2-ylcarbamate (0.46 g, 1.32 mmol) was dissolved into anhydrous DMF (10 mL), solid NaN3 (0.26 g, 4 mmol) was added and the reaction mixture was heated to 80° C. overnight. The reaction mixture was cooled to rt and diluted with EtOAc (100 mL) and water (30 mL). The organic phase was washed with water (3×30 mL), dried over Na2SO4 and evaporated. The residue was separated by chromatography on a silica gel column to give tert-butyl (2S,3S)-3-azido-1-cyclohexylbutan-2-ylcarbamate (0.215 g, 55%). 1H NMR (400 MHz, CDCl3): 4.38 (d, J=9.2 Hz, 1H), 3.72 (m, 1H), 3.60 (m, 1H), 1.82 (m, 1H), 1.67 (m, 4 h), 1.44 (s, 9H), 1.40-1.00 (m, 6H), 1.28 (d, J=6.4 Hz, 3H), 1.00-0.75 (m, 2H); MS (E/Z): 297 (M+H+).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to rt
  3. washThe organic phase was washed with water (3×30 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was separated by chromatography on a silica gel column

Sources & evidence

ORD record
ord-9786972ef17444a7981c67e779bf8b50
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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