Pyridine → 4-[(4,4'-Dimethoxytrityl)oxy]Butyric Acid, Triethylammonium Salt

HRID 411819Notes

Reaction equation

HRID 411819 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7](Cl)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[OH:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30].[N:32]1[CH:37]=[CH:36]C=[CH:34][CH:33]=1>>[CH2:33]([NH+:32]([CH2:24][CH3:3])[CH2:37][CH3:36])[CH3:34].[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7]([O:25][CH2:26][CH2:27][CH2:28][C:29]([O-:31])=[O:30])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 104134-Hydroxybutyric AcidHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Product 1

HCID 235087064-[(4,4'-Dimethoxytrityl)oxy]Butyric Acid, Triethylammonium Salt

Procedure

A solution of 4,4′-dimethoxytrityl chloride (695 mg, 2.05 mmol) and 4-hydroxybutyric acid (208 mg, 2.0 mmol) in anhydrous Pyridine (20 mL) was stirred overnight and concentrated to an oil in vacuo. The residue was dissolved in a mixture of MeOH and CH2Cl2 (95:5, v/v; 200 mL) and washed with 2M aqueous triethylammonium acetate (5×20 mL). The organic solution was evaporated, re-dissolved in CH2Cl2, dried over Na2SO4, and evaporated to give the crude title compound in a quantitative yield (1016 mg).

Workup

  1. concentrationconcentrated to an oil in vacuo
  2. dissolutionThe residue was dissolved in a mixture of MeOH and CH2Cl2 (95:5
  3. wash200 mL) and washed with 2M aqueous triethylammonium acetate (5×20 mL)
  4. customThe organic solution was evaporated
  5. dissolutionre-dissolved in CH2Cl2
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-29a474b3380747f7bde17e3c2984ec01
Source dataset
uspto-grants-2003_05
Patent number
US06559279B1

Reaction notes

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