Acetic Acid → HCID 68679184, compound

HRID 1172437Notes

Reaction equation

HRID 1172437 reaction equation
C([Li])CCC.[Si:6]([O:13][CH2:14][C:15]1[N:20]=[C:19]([N:21]=[C:22]2[N:26]([CH2:27][O:28][CH3:29])[CH:25]=[CH:24][S:23]2)[CH:18]=[CH:17][CH:16]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:40])(=O)=O)=CC=1.C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[Si:6]([O:13][CH2:14][C:15]1[N:20]=[C:19]([N:21]=[C:22]2[N:26]([CH2:27][O:28][CH3:29])[CH:25]=[C:24]([F:40])[S:23]2)[CH:18]=[CH:17][CH:16]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 588007N-FluorobenzenesulfonimideHCID 67055460HCID 67055460, compoundHCID 178418339Butyllithium

Product 1

HCID 68679184HCID 68679184, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

5 ml of tetrahydrofuran was cooled to −78° C., and then 1.05 ml of butyllithium (1.6 M, hexane solution) was dropped thereinto. Into the resulting reaction solution was dropped a solution of 280 mg of 6-(((tert-butyl(dimethyl)silyl)oxy)methyl)-N-(3-(methoxymethyl)thiazol-2(3H)-ylidene)pyridin-2-amine in 5 ml of tetrahydrofuran, followed by stirring at −78° C. for 30 minutes. A solution of N-fluorobenzenesulfonimide in 5 ml of tetrahydrofuran was dropped thereinto. After having the temperature of the resulting reaction solution allowed to −30° C., 230 μl of acetic acid was dropped thereinto. The resulting reaction solution was diluted with ethyl acetate, and then washed with water and brine. The resulting organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=3/1) to give the title compound.

Workup

  1. customInto the resulting reaction solution
  2. customthe temperature of the resulting reaction solution
  3. customallowed to −30° C.
  4. customThe resulting reaction solution
  5. washwashed with water and brine
  6. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-4aaee0c7a07d41c0ad1302120fafc85f
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

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