2-Hydroxyethyl 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-yl butanedioate → Cyclosporine TPGS

HRID 442622Notes

Reaction equation

HRID 442622 reaction equation
[CH3:1][CH2:2][C@@H:3]1[NH:46][C:44](=[O:45])[C@H:43]([C@H:47]([OH:54])[C@@H:48]([CH2:50]/[CH:51]=[CH:52]/[CH3:53])[CH3:49])[N:42]([CH3:55])[C:40](=[O:41])[C@H:39]([CH:56]([CH3:58])[CH3:57])[N:38]([CH3:59])[C:36](=[O:37])[C@H:35]([CH2:60][CH:61]([CH3:63])[CH3:62])[N:34]([CH3:64])[C:32](=[O:33])[C@H:31]([CH2:65][CH:66]([CH3:68])[CH3:67])[N:30]([CH3:69])[C:28](=[O:29])[C@@H:27]([CH3:70])[NH:26][C:24](=[O:25])[C@H:23]([CH3:71])[NH:22][C:20](=[O:21])[C@H:19]([CH2:72][CH:73]([CH3:75])[CH3:74])[N:18]([CH3:76])[C:16](=[O:17])[C@H:15]([CH:77]([CH3:79])[CH3:78])[NH:14][C:12](=[O:13])[C@H:11]([CH2:80][CH:81]([CH3:83])[CH3:82])[N:10]([CH3:84])[C:8](=[O:9])[CH2:7][N:6]([CH3:85])[C:4]1=[O:5].[CH3:86][C:87]1[C:92]([CH3:93])=[C:91]([O:94][C:95]([CH2:97][CH2:98][C:99]([O:101][CH2:102][CH2:103][OH:104])=[O:100])=[O:96])[C:90]([CH3:105])=[C:89]2[CH2:106][CH2:107][C:108]([CH2:111][CH2:112][CH2:113][CH:114]([CH2:116][CH2:117][CH2:118][CH:119]([CH2:121][CH2:122][CH2:123][CH:124]([CH3:126])[CH3:125])[CH3:120])[CH3:115])([CH3:110])[O:109][C:88]=12>C(O)C>[CH3:1][CH2:2][C@@H:3]1[NH:46][C:44](=[O:45])[C@H:43]([C@H:47]([OH:54])[C@@H:48]([CH2:50]/[CH:51]=[CH:52]/[CH3:53])[CH3:49])[N:42]([CH3:55])[C:40](=[O:41])[C@H:39]([CH:56]([CH3:57])[CH3:58])[N:38]([CH3:59])[C:36](=[O:37])[C@H:35]([CH2:60][CH:61]([CH3:62])[CH3:63])[N:34]([CH3:64])[C:32](=[O:33])[C@H:31]([CH2:65][CH:66]([CH3:68])[CH3:67])[N:30]([CH3:69])[C:28](=[O:29])[C@@H:27]([CH3:70])[NH:26][C:24](=[O:25])[C@H:23]([CH3:71])[NH:22][C:20](=[O:21])[C@H:19]([CH2:72][CH:73]([CH3:75])[CH3:74])[N:18]([CH3:76])[C:16](=[O:17])[C@H:15]([CH:77]([CH3:79])[CH3:78])[NH:14][C:12](=[O:13])[C@H:11]([CH2:80][CH:81]([CH3:83])[CH3:82])[N:10]([CH3:84])[C:8](=[O:9])[CH2:7][N:6]([CH3:85])[C:4]1=[O:5].[CH3:86][C:87]1[C:92]([CH3:93])=[C:91]([O:94][C:95]([CH2:97][CH2:98][C:99]([O:101][CH2:102][CH2:103][OH:104])=[O:100])=[O:96])[C:90]([CH3:105])=[C:89]2[CH2:106][CH2:107][C:108]([CH2:111][CH2:112][CH2:113][CH:114]([CH2:116][CH2:117][CH2:118][CH:119]([CH2:121][CH2:122][CH2:123][CH:124]([CH3:126])[CH3:125])[CH3:120])[CH3:115])([CH3:110])[O:109][C:88]=12

Participants

4

Reactant 2

HCID 714062-Hydroxyethyl 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-yl butanedioate3×HCID 5284373Cyclosporin A3×

Product 1

HCID 131721213Cyclosporine TPGS

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

200 mg of Cyclosporine was weighed into a 100 ml beaker and 1.2 grams of Vitamin E TPGS was added, and to this was added 8 grams of ethanol. The ethanol solvent, Cyclosporine, and TPGS were stirred at room temperature for 10 minutes until the Cyclosporine and TPGS components were clearly dissolved. The solvent was evaporated from a Petri dish overnight and the sample was examined under an Olympus BX50 microscope at 200× magnification by adding a small quantity of water to the cyclosporine/TPGS, and watching for visible crystals. No crystals were observed, only a clear solution was obtained. It was therefore concluded that solvent evaporation will also work to produce clear solutions of Cyclosporine/TPGS when added to water.

Workup

  1. additionwas added
  2. dissolutionwere clearly dissolved
  3. customThe solvent was evaporated from a Petri dish overnight
  4. additionby adding a small quantity of water to the cyclosporine/TPGS
  5. customonly a clear solution was obtained
  6. customIt was therefore concluded that solvent evaporation

Sources & evidence

ORD record
ord-cf4bd562a0e54fbb9f1accaee1a62c28
Source dataset
uspto-grants-1999_04
Patent number
US05891845

Reaction notes

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