Sodium Azide → (3S,5R)-3-Azidomethyl-5-methyl-octanoic acid tert-butyl ester

HRID 130538Notes

Reaction equation

HRID 130538 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][C@@H:8]([CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:9][C@H:10]([CH3:14])[CH2:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[N-:28]=[N+:29]=[N-:30].[Na+]>CS(C)=O.O>[C:1]([O:5][C:6](=[O:27])[CH2:7][C@@H:8]([CH2:15][N:28]=[N+:29]=[N-:30])[CH2:9][C@H:10]([CH3:14])[CH2:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 57178500(3S,5R)-5-Methyl-3-(toluene-4-sulfonyloxymethyl)-octanoic Acid Tert-butyl Ester

Product 1

HCID 57060687(3S,5R)-3-Azidomethyl-5-methyl-octanoic acid tert-butyl esterYield 79%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Tosylate 104 (2.92 g, 7.3 mmol) and sodium azide (1.43 g, 0.02 mol) were warmed to ˜50° C. in DMSO (30 mL). After 2 hours the solution was cooled to room temperature and diluted with water. The solution was extracted with ether and the combined organic phases dried (MgSO4) and concentrated to give an oil 1.54 g, 79%. Further purification by flash chromatography (95% hexane/EtOAc) gave an oil. [α]D=−8.3 (c 1 in CHCl3). 13C NMR (100 MHz; CDCl3) 172.01, 80.73, 54.89, 39.73, 39.46, 39.00, 33.40, 29.85, 28.30, 20.15, 19.82, 14.52.

Workup

  1. extractionThe solution was extracted with ether
  2. dry with materialthe combined organic phases dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2ed401cdd9a547f9a0188dd8c5be7871
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Reaction notes

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