Sodium → HCID 86588354, compound

HRID 2214803Notes

Reaction equation

HRID 2214803 reaction equation
C([O:9][C@H:10]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:12][C@@H:11]1[O:41][C@H:42]1[C@@H:60]([O:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C@H:59]([O:69][CH2:70][C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[C@@H:58]([CH2:77][O:78][CH2:79][C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)[O:57][C@@H:43]1[O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][C:53]([O:55][CH3:56])=[O:54])(=O)C1C=CC=CC=1.[Na]>C1(C)C=CC=CC=1.CO>[CH2:17]([O:16][C@H:15]1[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:12][C@H:11]([O:41][C@H:42]2[C@@H:60]([O:61][CH2:62][C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[C@H:59]([O:69][CH2:70][C:71]3[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=3)[C@@H:58]([CH2:77][O:78][CH2:79][C:80]3[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=3)[O:57][C@@H:43]2[O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][C:53]([O:55][CH3:56])=[O:54])[C@H:10]1[OH:9])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 86588355HCID 86588355, compound

Product 1

HCID 86588354HCID 86588354, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

540 mg (467 μmol) of compound 23 was dissolved in 5 ml of a methanol/dichloromethane 1/1 solvent mixture. Sodium (cat.) was then added to the mixture. After 1 hour at ambient temperature, the solution was neutralized with Amberlite resin IR 120 (H+). This was filtered and concentrated under vacuum. Chromatography of the crude product (elution: cyclohexane/ethyl acetate=2.75/1) yielded 442 mg (yield=90%) of product 24 in the form of a colorless oil.

Workup

  1. filtrationThis was filtered
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f5532528f0c54762b084514b372f68cf
Source dataset
uspto-grants-2006_09
Patent number
US07109182B2

Reaction notes

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