Cinchonidine → (S)-indole-3-succinic acid cinchonidine

HRID 353416

Reaction equation

HRID 353416 reaction equation
[CH2:1]=[CH:2][C@@H:3]1[C@@H:8]2[CH2:9][C@@H:10]([C@H:11]([OH:22])[C:12]3[CH:13]=[CH:14][N:15]=[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[N:5]([CH2:6][CH2:7]2)[CH2:4]1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH:32]([C:37]([OH:39])=[O:38])[CH2:33][C:34]([OH:36])=[O:35])=[CH:24]1>C(O)C>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C@@H:32]([C:37]([OH:39])=[O:38])[CH2:33][C:34]([OH:36])=[O:35])=[CH:24]1.[CH2:1]=[CH:2][C@@H:3]1[C@@H:8]2[CH2:9][C@@H:10]([C@H:11]([OH:22])[C:12]3[CH:13]=[CH:14][N:15]=[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[N:5]([CH2:6][CH2:7]2)[CH2:4]1

Participants

4

Reactant 2

HCID 101744CinchonidineHCID 5887082-(1H-indol-3-yl)butanedioic acid

Product 1

HCID 131724462(S)-indole-3-succinic acid cinchonidineYield 13.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.26 g (4.29 mmole) of cinchonidine and 1.00 g (4.29 mmole) of racemic indole-3-succinic acid in 10 mL of 96% ethanol was heated on a steam bath with magnetic stirring until all of the solid dissolved. The solution was cooled slowly to room temperature, and the white precipitate formed was collected and washed with ether. After 11 recrystallizations from 96% ethanol and one solution of 96% ethanol:methanol, 80:20 by volume, and drying, colorless fine needles of (S)-indole-3-succinic acid-cinchonidine salt was obtained. 0.296 g, yield: 13.1%, ee: 99.3%. Mp: 196-198° C. (with gas evolution). Elemental analysis: Calculated for C31H33N3O55: C=70.57%, H=6.30%, N=7.96% Found: C=70.00%; H=6.42%; N=7.84%. IR: 3500-2900, 1592, 1460 cm-1. By fractional removal of (S)-indole-3-succinic acid salt, followed by rotary evaporation of the solvent and recrystallization (supra vide), the (R)-indole-3-succinic acid-cinchonidine salt was obtained.

Workup

  1. temperaturewas heated on a steam bath
  2. dissolutiondissolved
  3. customthe white precipitate formed
  4. customwas collected
  5. washwashed with ether
  6. customAfter 11 recrystallizations from 96% ethanol and one solution of 96% ethanol
  7. dry with materialmethanol, 80:20 by volume, and drying

Sources & evidence

ORD record
ord-0aab0a77f3bc42828e79e7062857db87
Source dataset
uspto-grants-2004_06
Patent number
US06753297B2

Linked notes

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