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

HRID 442601Notes

Reaction equation

HRID 442601 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][C:10]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH2:18][OH:19])=[O:15])=[O:11])[C:5]([CH3:20])=[C:4]2[CH2:21][CH2:22][C:23]([CH2:26][CH2:27][CH2:28][CH:29]([CH2:31][CH2:32][CH2:33][CH:34]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH3:35])[CH3:30])([CH3:25])[O:24][C:3]=12.[CH3:42][CH2:43]/[C:44](/[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[C:45](/[C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][N+:61](C)([CH3:63])[CH3:62])=[CH:54][CH:53]=1)\[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[I-:71].[CH2:72](O)C.O=[Si]=O>O>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][C:10]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH2:18][OH:19])=[O:15])=[O:11])[C:5]([CH3:20])=[C:4]2[CH2:21][CH2:22][C:23]([CH2:26][CH2:27][CH2:28][CH:29]([CH2:31][CH2:32][CH2:33][CH:34]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH3:35])[CH3:30])([CH3:25])[O:24][C:3]=12.[CH3:42][CH2:43]/[C:44](/[C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1)=[C:45](/[C:52]1[CH:53]=[CH:54][C:55]([O:58][CH2:59][CH2:60][N:61]([CH3:63])[CH3:62])=[CH:56][CH:57]=1)\[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[CH3:72][I:71]

Participants

7

Reactant 4

HCID 702EthanolHCID 24261SilicaHCID 714062-Hydroxyethyl 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-yl butanedioateHCID 3033898Ethanaminium, 2-(4-((1Z)-1,2-diphenyl-1-buten-1-yl)phenoxy)-N,N,N-trimethyl-, iodide (1:1)

Product 2

HCID 714062-Hydroxyethyl 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-yl butanedioateHCID 21150887Tamoxifen methyliodide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

TPGS (500 mg) was melted at 40°-60° C. in a water bath. Tamoxifen methiodide (100 mg, from Pharmos Corp., FL., USA) was added to the melted material and the mixture was agitated for several minutes. A small amount of absolute ethanol (up to 5%, v/v) was added in order to get an homogeneous mixture. PVP (Kollidon PF 12, 2.6 ml of a 10% solution in water) was then added and the mixture was agitated again for several minutes. Cab-O-Sil (2.8 ml of a 5% solution in water) was added and the mixture was agitated again for several minutes. The resultant TPGS/PVP/Tamoxifen methiodide mixture was then freeze-dried overnight using a Christ beta lyophilizer (Germany). A powdered free-flowing TPGS/PVP/Tamoxifen methyliodide coprecipitate quickly dispersible in water was obtained.

Workup

  1. customto get an homogeneous mixture
  2. stirringthe mixture was agitated again for several minutes
  3. stirringthe mixture was agitated again for several minutes
  4. dry with materialThe resultant TPGS/PVP/Tamoxifen methiodide mixture was then freeze-dried overnight

Sources & evidence

ORD record
ord-300adfcd2094433eafaa2254c9b76d4a
Source dataset
uspto-grants-1999_04
Patent number
US05891469

Reaction notes

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