Carbon Dioxide → Triethylammonium hydrogen carbonate

HRID 1375298Notes

Reaction equation

HRID 1375298 reaction equation
[C:1](#[N:3])[CH3:2].[CH:4](C1C=CC=CC=1C=C)=[CH2:5].[CH2:14]=[CH:15]C1C=CC=CC=1.[C:22](=[O:24])=[O:23].[OH2:25]>C(N(CC)CC)C.C(O)(=O)C.O1CCCC1.CO>[C:22](=[O:25])([OH:24])[O-:23].[CH2:1]([NH+:3]([CH2:14][CH3:15])[CH2:4][CH3:5])[CH3:2]

Participants

10

Reactant 5

HCID 280Carbon DioxideHCID 962Water2×HCID 6342AcetonitrileHCID 7501StyreneHCID 666661,2-Diethenylbenzene

Product 1

HCID 11768884Triethylammonium hydrogen carbonate

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

Acetonitrile (HPLC gradient-grade), divinylbenzene (synthesis grade), methanol (HPLC gradient-grade), styrene (synthesis grade), and tetrahydrofuran (analytical reagent grade) were obtained from Merck (Darmstadt, Germany). Styrene and divinylbenzene were distilled before use. Acetic acid (analytical reagent grade), azobisisobutyronitrile (synthesis grade), decanol (synthesis grade), and triethylamine (p.a.) were purchased from Fluka (Buchs, Switzerland). A 1.0 M stock solution of triethylammonium acetate (TEM) was prepared by dissolving equimolar amounts of triethylamine and acetic acid in water. A 0.50 M stock solution of triethylammonium bicarbonate (TEAB) was prepared by passing carbon dioxide gas (AGA, Vienna, Austria) through a 0.50 M aqueous solution of triethylamine at 5° C. until pH 8.4–8.9 was reached. For preparation of all aqueous solutions, high-purity water (Epure, Barnstead Co., Newton, Mass., USA) was used. The standards of phosphorylated and non-phosphorylated oligodeoxynucleotides ((dT)12-18, p(dT)12-18, p(dT)19-24, p(dT)25-30) were purchased as sodium salts from Pharmacia (Uppsala, Sweden) or Sigma-Aldrich (St. Louis, Mo., USA). The synthetic oligodeoxynucleotides (dT)24 (Mr 7,238.71), a 5′-dimethoxytritylated 5-mer (DMTr-ATGCG, Mr 1805.42), and an 80-mer (Mr 24,527.17):

Workup

  1. distillationStyrene and divinylbenzene were distilled before use
  2. customA 1.0 M stock solution of triethylammonium acetate (TEM) was prepared
  3. customat 5° C.

Sources & evidence

ORD record
ord-781732ec89ac4952a011eab5785ed456
Source dataset
uspto-grants-2007_01
Patent number
US07169298B2

Reaction notes

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