2-Cyanoethyl tetraisopropylphosphorodiamidite → N-biotinyl-aminopropyl 2-cyanoethyl N,N-diisopropylphosphoramidite

HRID 1165364

反応式

HRID 1165364 の反応式
[C:1]([NH:16][CH:17](O)[CH2:18][CH3:19])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:14]2[C@@H:9]([NH:10][C:11]([NH:13]2)=[O:12])[CH2:8][S:7]1.N1[C-]=NN=N1.C([NH2+]C(C)C)(C)C.[CH:33]([N:36]([CH:50]([CH3:52])[CH3:51])[P:37](N(C(C)C)C(C)C)[O:38][CH2:39][CH2:40][C:41]#[N:42])([CH3:35])[CH3:34].C(=O)(O)[O-:54].[Na+]>CN(C=O)C>[CH:33]([N:36]([CH:50]([CH3:52])[CH3:51])[P:37]([O:38][CH2:39][CH2:40][C:41]#[N:42])[O:54][CH2:19][CH2:18][CH2:17][NH:16][C:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:14]2[C@@H:9]([NH:10][C:11]([NH:13]2)=[O:12])[CH2:8][S:7]1)([CH3:35])[CH3:34]

参加物

6

反応物 4

HCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 516892Sodium BicarbonateHCID 131716340N-biotinylaminopropanolHCID 178458033HCID 178458033、化合物

生成物 1

HCID 15085419N-biotinyl-aminopropyl 2-cyanoethyl N,N-diisopropylphosphoramidite

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 150 mg of N-biotinylaminopropanol (2b) in 5 ml of dry DMF was added 65 mg of diisopropylammonium tetrazolide and 0.300 ml of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite. The resulting solution was stirred at room temperature for 1.0 hr and then poured onto 50 ml of 5% aqueous sodium bicarbonate. The mixture was extracted with two 50 ml portions of methylene chloride, and the combined extracts were washed with 5% sodium bicarbonate and brine, dried over sodium sulfate, and evaporated to afford the crude product as a thick oil. This was dissolved in 2 ml of dry methylene chloride affording a solution that was added dropwise to 30 ml of rapidly stirring petroleum ether. The colorless precipitate which formed was collected by suction filtration under argon, affording after drying at room temperature under vacuum 151 mg (60%) of a colorless solid.

後処理

  1. extractionThe mixture was extracted with two 50 ml portions of methylene chloride
  2. washthe combined extracts were washed with 5% sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

出典と根拠

ORDレコード
ord-7164f27389e64b539be65359be962472
出典データセット
uspto-grants-1990_03
特許番号
US04908453

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