1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 131731287, compound

HRID 2361733Notes

Reaction equation

HRID 2361733 reaction equation
[C:1]([N:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH2:20][OH:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[CH3:25][O:26][C:27]1[CH:48]=[CH:47][C:30]([C:31](Cl)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:29][CH:28]=1.C(Cl)(Cl)Cl.CO>N1C=CC=CC=1>[C:1]([C:31]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)[C:30]1[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:48][CH:47]=1)([O:3][CH2:4][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:2].[NH:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH2:20][OH:21]

Participants

5

Reactant 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 688635Fmoc-L-Prolinol3×HCID 21584188Chloroform methanol

Product 1

HCID 131731287HCID 131731287, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The Fmoc-L-prolinol (Compound 2) (1.4 g, 4.3 mmol) was dissolved in 20 ml of pyridine and azeotroped three times. The residual substance obtained was dissolved in 20 ml of pyridine. While stirring this solution in an ice bath under argon, 4,4′-dimethoxytrityl chloride (DMTr-Cl) (1.8 g, 5.3 mmol) was added thereto. The reaction in this reaction solution was followed by TLC using chloroform/methanol, and the reaction was allowed to proceed for 4 hours until a spot of the Fmoc-L-prolinol no longer was observed. In order to quench excess DMTr-Cl, 3 ml of methanol was added to the reaction solution, and this was stirred for 10 minutes. Chloroform was further added to the reaction solution, and thereafter, an organic layer was collected. The collected organic layer was washed with saturated saline, then with a 5% aqueous solution of sodium hydrogencarbonate, and again with saturated saline. The organic layer thus washed was dried with anhydrous sodium sulfate. The organic layer then was filtered, and the filtrate obtained was vacuum concentrated. The residual substance obtained was purified by silica gel column chromatography (the eluent: chloroform, 1% pyridine). Thus, Compound 3 was obtained (2.0 g, yield: 74%). The result of NMR analysis with respect to this compound is shown below.

Workup

  1. customazeotroped three times
  2. customThe residual substance obtained
  3. customThe reaction in this reaction solution
  4. customIn order to quench excess DMTr-Cl, 3 ml of methanol
  5. additionwas added to the reaction solution
  6. stirringthis was stirred for 10 minutes
  7. additionChloroform was further added to the reaction solution
  8. customan organic layer was collected
  9. washThe collected organic layer was washed with saturated saline
  10. washThe organic layer thus washed
  11. dry with materialwas dried with anhydrous sodium sulfate
  12. filtrationThe organic layer then was filtered
  13. customthe filtrate obtained
  14. concentrationconcentrated
  15. customThe residual substance obtained
  16. customwas purified by silica gel column chromatography (the eluent

Sources & evidence

ORD record
ord-4a42397814874002b58e721b69483448
Source dataset
uspto-grants-2014_04
Patent number
US08691782B2

Reaction notes

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