Fumaric Acid → HCID 9874450, compound

HRID 636060Notes

Reaction equation

HRID 636060 reaction equation
[C:1]([CH:5]1[C:10](CCCC)([OH:11])[C:9]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:8][C:7]([C@H:20]2[N:24]([CH2:25][CH2:26][CH2:27][N:28]([CH3:41])[CH2:29][CH2:30][O:31][C:32]3[CH:37]=[CH:36][C:35]4[O:38][CH2:39][O:40][C:34]=4[CH:33]=3)[C:23](=[O:42])[CH2:22][S:21]2)=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].[C:43]([OH:50])(=[O:49])/[CH:44]=[CH:45]/[C:46]([OH:48])=[O:47]>C(O)C>[C:43]([OH:50])(=[O:49])/[CH:44]=[CH:45]/[C:46]([OH:48])=[O:47].[C:16]([C:9]1[CH:8]=[C:7]([C@H:20]2[N:24]([CH2:25][CH2:26][CH2:27][N:28]([CH3:41])[CH2:29][CH2:30][O:31][C:32]3[CH:37]=[CH:36][C:35]4[O:38][CH2:39][O:40][C:34]=4[CH:33]=3)[C:23](=[O:42])[CH2:22][S:21]2)[CH:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[C:10]=1[OH:11])([CH3:17])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 86756447HCID 86756447, compound

Product 1

HCID 9874450HCID 9874450, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of (S)-(−)-2-(3,5-di-tert-butyl-4-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-(3,4-methylenedioxy-phenoxy)ethyl]amino]propyl]-1,3-thiazolidin-4-one (380 mg, 0.70 mmol) synthesized according to the process described in JP No. 6-206842/1994 in ethanol (10 ml) was added a solution of fumaric acid (65 mg, 0.56 mmol) in ethanol (10 ml) (prepared under preheating) and the mixture was stirred, then the solvent was removed under reduced pressure. The residue was combined with n-hexane and cooled in a freezer for 4 hours, then ether was added. The precipitate was filtered off and dried to give a white amorphous powder of the fumaric acid salt (300 mg). To a solution of this powder (52 mg) in acetone (1 ml) was added water (3 ml), and the mixture was heated under reflux for 10 minutes, then stirred at room temperature overnight. The resulting precipitate was filtered with suction, washed with water and dried to give white crystals (36.5 mg). mp: 109-117° C. Elementary analysis: calculated for C34H46N2O9.H2O: C, 60.34, H, 7.15, N, 4.14; found: C, 60.52, H, 6.84, N, 4.19.

Workup

  1. customthe solvent was removed under reduced pressure
  2. temperaturecooled in a freezer for 4 hours
  3. additionether was added
  4. filtrationThe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-3157058e4aad47718cb0181de01cd454
Source dataset
uspto-grants-2001_02
Patent number
US06191281B1

Reaction notes

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