Fumaric Acid → HCID 9874450, compound

HRID 636061Notes

Reaction equation

HRID 636061 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C@H: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])[CH2:18][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].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43]>C(OCC)(=O)C.CO>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43].[C:12]([C:9]1[CH:8]=[C:7]([C@H: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])[CH2:18][S:17]2)[CH:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 9874451HCID 9874451, compound

Product 1

HCID 9874450HCID 9874450, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-(−)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-(3,4-methylenedioxy-phenoxy)ethyl]amino]propyl]-1,3-thiazolidin-4-one (569 mg, 1.05 mmol) in ethyl acetate (2 ml) was added a solution of fumaric acid (116 mg, 1.00 mmol) in methanol (3 ml) (prepared under preheating) and the mixture was stirred, then the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (1 ml) under heating and the mixture was stirred at room temperature for 15 hours. The precipitate was filtered off, washed with ethyl acetate:n-hexane (1:1) and dried to give white crystals (582 mg). mp: 142-144° C.; Elementary analysis: calculated for C34H46N2O9: C, 61.99, H, 7.04, N, 4.25; found: C, 61.77, H, 7.09, N, 4.07.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (1 ml)
  3. temperatureunder heating
  4. stirringthe mixture was stirred at room temperature for 15 hours
  5. filtrationThe precipitate was filtered off
  6. washwashed with ethyl acetate:n-hexane (1:1)
  7. customdried

Sources & evidence

ORD record
ord-539626794cb94a8081219ca2e25a348e
Source dataset
uspto-grants-2001_02
Patent number
US06191281B1

Reaction notes

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