Hydrochloric Acid → Alpha-Lipoic Acid Alpha Cyclodextrin

HRID 16915Notes

Reaction equation

HRID 16915 reaction equation
[OH-].[K+].[CH2:3]1[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[S:6][S:5][CH2:4]1.[CH2:15]([OH:80])[C@H:16]1[O:21][C@@H:20]2[O:22][C@H:23]3[C@H:28]([OH:29])[C@@H:27]([OH:30])[C@@H:26]([O:31][C@H:32]4[C@H:37]([OH:38])[C@@H:36]([OH:39])[C@@H:35]([O:40][C@H:41]5[C@H:46]([OH:47])[C@@H:45]([OH:48])[C@@H:44]([O:49][C@H:50]6[C@H:55]([OH:56])[C@@H:54]([OH:57])[C@@H:53]([O:58][C@H:59]7[C@H:65]([OH:66])[C@@H:64]([OH:67])[C@@H:62]([O:63][C@H:17]1[C@H:18]([OH:79])[C@H:19]2[OH:78])[O:61][C@@H:60]7[CH2:68][OH:69])[O:52][C@@H:51]6[CH2:70][OH:71])[O:43][C@@H:42]5[CH2:72][OH:73])[O:34][C@@H:33]4[CH2:74][OH:75])[O:25][C@@H:24]3[CH2:76][OH:77].Cl>O>[CH2:3]1[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[S:6][S:5][CH2:4]1.[CH2:70]([OH:71])[C@H:51]1[O:52][C@@H:53]2[O:58][C@H:59]3[C@H:65]([OH:66])[C@@H:64]([OH:67])[C@@H:62]([O:63][C@H:17]4[C@H:18]([OH:79])[C@@H:19]([OH:78])[C@@H:20]([O:22][C@H:23]5[C@H:28]([OH:29])[C@@H:27]([OH:30])[C@@H:26]([O:31][C@H:32]6[C@H:37]([OH:38])[C@@H:36]([OH:39])[C@@H:35]([O:40][C@H:41]7[C@H:46]([OH:47])[C@@H:45]([OH:48])[C@@H:44]([O:49][C@H:50]1[C@H:55]([OH:56])[C@H:54]2[OH:57])[O:43][C@@H:42]7[CH2:72][OH:73])[O:34][C@@H:33]6[CH2:74][OH:75])[O:25][C@@H:24]5[CH2:76][OH:77])[O:21][C@@H:16]4[CH2:15][OH:80])[O:61][C@@H:60]3[CH2:68][OH:69]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 864alpha Lipoic acidHCID 14797Potassium Hydroxide2×HCID 444913Alpha-Cyclodextrin

Product 1

HCID 131728183Alpha-Lipoic Acid Alpha Cyclodextrin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

186.7 g of a 45% potassium hydroxide solution (1.498 moles) was added to 3910 g water and mixed at room temperature until clear. 300 g alpha-lipoic acid (99%, 1.439 moles) was added to the potassium hydroxide solution and mixed until clear clear (in case of the presence of amorphous silica as flowing agent the solution will be slightly cloudy). 1,572 g alpha cyclodextrin (at 9.25% water 1.468 moles) was added and stirred for 3 hours at room temperature until no further clarification was seen. 1.498 moles of 37% hydrochloric acid was added to precipitate the complex. With a minimal molar excess of hydrochloric acid in comparison to the potassium hydroxide used, the final pH of the solution was at pH 3. The final aqueous mixture was spray dried immediately at 180° C.

Workup

  1. additionmixed at room temperature until clear
  2. additionmixed until clear clear (in case of the presence of amorphous silica
  3. customto precipitate the complex
  4. customdried immediately at 180° C.

Sources & evidence

ORD record
ord-831ed8ef8b6d4e60a3a83e6bed16fb6d
Source dataset
uspto-grants-2010_06
Patent number
US07737269B2

Reaction notes

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