Toluene → HCID 86602929, compound

HRID 1868172Notes

Reaction equation

HRID 1868172 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:41]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C@H:40]([O:50][C@@H:51]2[O:80][C@H:79]([CH3:81])[C@@H:70]([O:71][CH2:72][C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)[C@H:61]([O:62][CH2:63][C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[C@H:52]2[O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C@@H:39]([CH2:82][O:83][CH2:84][C:85]2[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=2)[O:38][CH:10]1[O:11][C@@H:12]1[C@@H:19]2[C@@H:15]([N:16]([C:20]([O:22][CH2:23]C3C=CC=CC=3)=[O:21])[O:17][CH2:18]2)[CH2:14][C@H:13]1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C[O-].[Na+].C(OCC)C>CO>[CH2:1]([O:8][C@@H:9]1[C@@H:41]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C@H:40]([O:50][C@@H:51]2[O:80][C@H:79]([CH3:81])[C@@H:70]([O:71][CH2:72][C:73]3[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=3)[C@H:61]([O:62][CH2:63][C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[C@H:52]2[O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C@@H:39]([CH2:82][O:83][CH2:84][C:85]2[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=2)[O:38][C@@H:10]1[O:11][C@@H:12]1[C@@H:19]2[C@@H:15]([N:16]([C:20]([O:22][CH3:23])=[O:21])[O:17][CH2:18]2)[CH2:14][C@H:13]1[O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 10942334Sodium MethoxideHCID 86602930HCID 86602930, compound

Product 1

HCID 86602929HCID 86602929, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The compound (516 mg, 0.42 mmol) synthesized in Example 6 (6i) was dissolved in methanol (6 mL) and toluene (6 mL) and sodium methoxide (221 μL, 1.15 mmol) was added thereto, followed by stirring of the mixture at 50° C. for 40 minutes. After cooling to room temperature, Dowex 50W×8 was added thereto until the reaction mixture became neutral and it was filtered, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:diethyl ether, 1.5:1-1:1, v/v) to obtain the desired title compound (173 mg, yield 47%) as colorless amorphous matter.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationit was filtered
  3. distillationby distilling off of the solvent under reduced pressure
  4. customThe residue was purified

Sources & evidence

ORD record
ord-3a806330978e4389b1ed86c4c73519ab
Source dataset
uspto-grants-2009_12
Patent number
US07632930B2

Reaction notes

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