Phosphate → HCID 23449150, compound

HRID 1839322Notes

Reaction equation

HRID 1839322 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[N:8]=[CH:9][N:10]2[CH:14]=[CH:13][S:12][C:11]=12)(=[O:4])=[O:3].C([Li])CCC.CCCCCC.[CH2:26]([Sn:30](Cl)([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH3:29].P([O-])([O-])([O-])=O>CN(P(N(C)C)(N(C)C)=O)C.C1COCC1>[CH3:1][S:2]([NH:5][CH2:6][C:7]1[N:8]=[CH:9][N:10]2[CH:14]=[C:13]([Sn:30]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:26][CH2:27][CH2:28][CH3:29])[S:12][C:11]=12)(=[O:3])=[O:4]

Participants

7

Reactant 4

HCID 1061PhosphateHCID 15096Tributyltin Chloride2×HCID 17811098HCID 17811098, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 23449150HCID 23449150, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 231 mg of 7-(methanesulfonylaminomethyl)imidazo[5,1-b]thiazole dissolved in a mixed solution composed of 10 ml of dry THF and 1 ml of dry HMPA was cooled to −5° C. with stirring. A 1.6 N n-butyllithium/n-hexane solution (2.0 ml) was added dropwise to the mixed solution in an argon atmosphere at −51 to −49° C. over a period of 15 min . The mixture was stirred at the same temperature for 15 min. Further, 0.34 ml of tri-n-butylstannyl chloride was added dropwise thereto at −50 to −48° C. over a period of 10 min. The mixture was stirred at −50 to −40° C. for 140 min. Tri-n-butylstannyl chloride (0.07 ml) was additionally added to the reaction solution at −42° C. The mixture was stirred for 30 min. 0.38 M phosphate buffer (pH 6.0) (15 ml) was added thereto. The mixed solution was extracted with 30 ml of ethyl acetate. The organic layer was washed with 0.38 M phosphate buffer (pH 6.0) and saturated brine in that order, and then dried over anhydrous sodium sulfate. The anhydrous magnesium sulfate was removed by filtration. The solvent was removed by distillation. The brown oil thus obtained was purified by column chromatography on silica gel (eluting with dichloromethane:ethyl acetate=1:1 and then with ethyl acetate only) to give 160 mg of the title compound as a yellow crystal.

Workup

  1. stirringThe mixture was stirred at the same temperature for 15 min
  2. stirringThe mixture was stirred at −50 to −40° C. for 140 min
  3. stirringThe mixture was stirred for 30 min
  4. extractionThe mixed solution was extracted with 30 ml of ethyl acetate
  5. washThe organic layer was washed with 0.38 M phosphate buffer (pH 6.0) and saturated brine in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe anhydrous magnesium sulfate was removed by filtration
  8. customThe solvent was removed by distillation
  9. customThe brown oil thus obtained
  10. customwas purified by column chromatography on silica gel (
  11. washeluting with dichloromethane

Sources & evidence

ORD record
ord-86583def5b694bd690908feed646f555
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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