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 348250Notes

Reaction equation

HRID 348250 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-1189d048870549e1ba60c5f465d1f061
Source dataset
uspto-grants-2007_02
Patent number
US07176235B2

Reaction notes

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