4-Toluenesulfonyl chloride → HCID 59645193, compound

HRID 2252536Notes

Reaction equation

HRID 2252536 reaction equation
[CH2:1](N(CC)CC)C.S(Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=O)=O.[C:19](=[O:22])([O-:21])[O-].[K+].[K+].[CH2:25]([O:27][C:28](=[O:34])[CH2:29][NH:30][CH2:31][CH:32]=[CH2:33])[CH3:26]>O1CCCC1.C(#N)C.O.C(O)C>[CH2:25]([O:27][C:28](=[O:34])[CH2:29][N:30]([CH2:31][CH:32]=[CH2:33])[CH2:15][C:14]1[CH:16]=[CH:17][CH:11]=[C:12]([O:21][CH2:19][O:22][CH3:1])[CH:13]=1)[CH3:26]

Participants

9

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 10975597N-2-Propen-1-ylglycine ethyl ester

Product 1

HCID 59645193HCID 59645193, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the compound prepared in Reference Example 2 in tetrahydrofuran (16 mL) were added triethylamine (2.0 mL) and tosyl chloride (0.72 mL) at 0° C. and the mixture was stirred for 40 minutes at 0° C. Ethanol (0.23 mL) was added to the reaction mixture, which was stirred for 20 minutes at 0° C. A solution of acetonitrile (5.0 mL), potassium carbonate (2.16 g) and N-allylglycine ethyl ester (1.68 g) in acetonitrile (18 mL) was added to the reaction mixture, which was stirred for 40 minutes at 75° C. The reaction mixture was cooled to room temperature, then poured into cold water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:1→6:1) to give the title compound (1.84 g) having the following physical data.

Workup

  1. stirringwas stirred for 20 minutes at 0° C
  2. stirringwas stirred for 40 minutes at 75° C
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:1→6:1)

Sources & evidence

ORD record
ord-003a461fb6b54ea3adc573dc66eb958c
Source dataset
uspto-grants-2008_01
Patent number
US07323456B2

Reaction notes

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