Hydrochloric Acid → HCID 53895150, compound

HRID 609887Notes

Reaction equation

HRID 609887 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]2[N:20]([CH2:21][CH2:22][CH2:23][N:24]([CH3:37])[CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]4[O:34][CH2:35][O:36][C:30]=4[CH:29]=3)[C:19](=[O:38])[CH:18]([CH2:39][C:40]([O:42]CC)=[O:41])[S:17]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C(O)C.O>[C:12]([C:9]1[CH:8]=[C:7]([CH:16]2[N:20]([CH2:21][CH2:22][CH2:23][N:24]([CH3:37])[CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]4[O:34][CH2:35][O:36][C:30]=4[CH:29]=3)[C:19](=[O:38])[CH:18]([CH2:39][C:40]([OH:42])=[O:41])[S:17]2)[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 544079592-(3, 5-Di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-(3,4-methylenedioxyphenoxy)ethyl]amino]-propyl]-5-ethoxycarbonylmethyl-1,3-thiazolidin-4-one

Product 1

HCID 53895150HCID 53895150, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

In ethanol (5 ml) was dissolved 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-(3,4-methylenedioxyphenoxy)ethyl]amino]propyl]-5-ethoxycarbonylmethyl-1,3thiazolidin-4-one (100 mg) prepared in Example 46, and a solution of sodium hydroxide (200 mg) in 20% water-containing ethanol was added, then the mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was neutralized with 1N hydrochloric acid and concentrated under reduced pressure. To the residue was added a mixture of water (50 ml) and chloroform (50 ml), and the mixture was stirred. The organic layer was separated, washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was triturated with n-hexane to afford 80 mg (84%) of the title compound as a pale yellow solid. NMR (CDCl3) (200 MHz) δ: 1.41 (18/2H, s), 1.42 (18/2H, s), 1.4-2.4 (2H, m), 2.85 (3/2H, s), 2.90 (3/2H, s), 2.7-3.8 (8H, m), 4.1-4.7 (3H, m), 5.2-5.4 (1H, m), 5.66 (1/2H, brs), 5.81 (1/2H, brs), 5.89 (2H, s), 6.2-6.7 (3H, m), 7.13 (2/2H, s), 7.14 (2/2H, s)

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added
  5. additiona mixture of water (50 ml) and chloroform (50 ml)
  6. stirringthe mixture was stirred
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-fa871386fe184b8b8c3d5c8d14f38f4b
Source dataset
uspto-grants-1999_12
Patent number
US05998452

Reaction notes

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