p-Toluenesulfonic acid monohydrate → HCID 10019486, compound

HRID 1870062Notes

Reaction equation

HRID 1870062 reaction equation
C(OC([N:8]1[C:12]([CH3:32])([C:13]2[NH:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:20][CH:19]=3)=[CH:16][N:17]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.CC1C=CC(S(O)(=O)=O)=CC=1.O>CO>[NH2:8][C:12]([C:13]1[NH:14][C:15]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:23]=2)=[CH:16][N:17]=1)([CH3:32])[CH2:11][OH:10]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11385847HCID 11385847, compound

Product 1

HCID 10019486HCID 10019486, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a flame dried round bottom flask equipped with a magnetic stirbar under an inert atmosphere was added 6 (973 mg, 2.07 mmol) followed by MeOH (20 mL) and p-TsOH.H2O (1.22 g, 6.42 mmol). This mixture was then heated to reflux, stirred 3 hours, cooled to 0° C., and quenched by slow addition of saturated aqueous NaHCO3 (20 mL). This solution was then diluted with EtOAc (30 mL) and the aqueous layer was discarded. The organic phase was washed with saturated aqueous NaHCO3 (1×20 mL), washed with 1M NaOH (1×20 mL), dried over sodium sulfate, and concentrated to an orange oil. To this oil was added Et2O which produced VPC24241 (408 mg, 60%) as a white precipitate which was collected by filtration.

Workup

  1. customTo a flame dried round bottom flask
  2. customequipped with a magnetic stirbar under an inert atmosphere
  3. temperatureThis mixture was then heated
  4. temperatureto reflux
  5. customquenched by slow addition of saturated aqueous NaHCO3 (20 mL)
  6. additionThis solution was then diluted with EtOAc (30 mL)
  7. washThe organic phase was washed with saturated aqueous NaHCO3 (1×20 mL)
  8. washwashed with 1M NaOH (1×20 mL)
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated to an orange oil
  11. additionTo this oil was added Et2O which

Sources & evidence

ORD record
ord-f1128dcc63c64112b5dc58a1a0c04335
Source dataset
uspto-grants-2009_12
Patent number
US07638637B2

Reaction notes

Loading…