Hydrochloric Acid → Alpha-Lipoic Acid Alpha Cyclodextrin

HRID 16917Notes

Reaction equation

HRID 16917 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

23.9 g of a 45% potassium hydroxide solution (0.192 moles) was added to 767 g water and mixed at room temperature until clear. 40.0 g alpha-lipoic acid (98%, 0.190 moles) was added to the potassium hydroxide solution and mixed at room temperature until clear (in case of the presence of amorphous silica as flowing agent the solution will be slightly cloudy). 221.7 g alpha cyclodextrin (9.2% water content, 0.207 moles) was added and stirred for 60 minutes at room temperature. 0.192 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 about pH 3. The final aqueous mixture is spray dried immediately at 180° C.

Workup

  1. additionmixed at room temperature until clear
  2. additionmixed at room temperature until 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-db50c57ccac04da18f71f240ba724e5e
Source dataset
uspto-grants-2010_06
Patent number
US07737269B2

Reaction notes

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