Hydrochloric Acid → HCID 54002400, compound

HRID 582628Notes

Reaction equation

HRID 582628 reaction equation
C([O:8][C:9]1[C:10]([CH3:42])=[C:11]2[C:16](=[C:17]([CH3:20])[C:18]=1[CH3:19])[O:15][C:14]([CH2:22][N:23]([CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]=[C:35]3[S:39][C:38](=[O:40])[NH:37][C:36]3=[O:41])=[CH:30][CH:29]=1)[CH3:24])([CH3:21])[CH2:13][CH2:12]2)C1C=CC=CC=1.Cl>C(O)(=O)C>[OH:8][C:9]1[C:10]([CH3:42])=[C:11]2[C:16](=[C:17]([CH3:20])[C:18]=1[CH3:19])[O:15][C:14]([CH2:22][N:23]([CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([CH:34]=[C:35]3[S:39][C:38](=[O:40])[NH:37][C:36]3=[O:41])=[CH:32][CH:33]=1)[CH3:24])([CH3:21])[CH2:13][CH2:12]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53935530HCID 53935530, compound

Product 1

HCID 54002400HCID 54002400, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 12.5 g of the product obtained in example 1, in 120 ml of acetic acid was added 40 ml of concentrated hydrochloric acid. The resulting mixture was heated at 60° C. for 1 h. At the end of this time, the solvent was removed under reduced pressure and the residue was diluted with acetone. The resulting white solid was filtered and washed with excess of acetone. The solid was suspended in methanol and the pH was adjusted to 7 by the addition of triethylamine. The solvent was removed under reduced pressure and the resulting residue was dissolved in ethyl acetate and washed with water followed by brine. The organic layer was dried over anhydrous sodium sulphate and the solvent was removed by distillation under reduced pressure. The crude product was purified by column chromatography on silicagel using 2 to 10% (gradient elution) of methanol in chloroform to afford 9.8 g of the title compound.

Workup

  1. customAt the end of this time, the solvent was removed under reduced pressure
  2. additionthe residue was diluted with acetone
  3. filtrationThe resulting white solid was filtered
  4. washwashed with excess of acetone
  5. additionthe pH was adjusted to 7 by the addition of triethylamine
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe resulting residue was dissolved in ethyl acetate
  8. washwashed with water
  9. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  10. customthe solvent was removed by distillation under reduced pressure
  11. customThe crude product was purified by column chromatography on silicagel

Sources & evidence

ORD record
ord-85b9aabcccc24aa8997e107b10abe20c
Source dataset
uspto-grants-1999_07
Patent number
US05925656

Reaction notes

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