1,8-Diazabicyclo(5.4.0)undec-7-ene → (5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene

HRID 1357413Notes

Reaction equation

HRID 1357413 reaction equation
O[C@@H:2]([C:8]([CH3:16])=[CH:9][C:10]1[N:11]=[C:12]([CH3:15])[S:13][CH:14]=1)[CH2:3][CH:4]=[C:5]([I:7])[CH3:6].C1(P([N:31]=[N+:32]=[N-:33])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:31]([C@H:2]([C:8]([CH3:16])=[CH:9][C:10]1[N:11]=[C:12]([CH3:15])[S:13][CH:14]=1)[CH2:3][CH:4]=[C:5]([I:7])[CH3:6])=[N+:32]=[N-:33]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 86586610(5R)-5-hydroxy-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene

Product 1

HCID 86586612(5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (5R)-5-hydroxy-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene (1.74 g) in 30 mL of toluene is cooled to 0° C. and treated with diphenylphosphoryl azide (1.65 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.91 g) for 2 hours. The mix is warmed to ambient temperature and diluted with ethyl acetate. The solution is washed sequentially with water, sat. NaHCO3, and brine, then dried over MgSO4, filtered, and evaporated. The product is purified by SiO2 chromatography (7.5% ethyl acetate/hexanes).

Workup

  1. washThe solution is washed sequentially with water, sat. NaHCO3, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe product is purified by SiO2 chromatography (7.5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-151492d8b6b1444dab5dd8c382c0f33f
Source dataset
uspto-grants-2003_07
Patent number
US06589968B2

Reaction notes

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