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

HRID 1165363노트

반응식

HRID 1165363 반응식
[C:1]([NH:16][CH:17](O)[CH3:18])(=[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:32]([N:35]([CH:49]([CH3:51])[CH3:50])[P:36](N(C(C)C)C(C)C)[O:37][CH2:38][CH2:39][C:40]#[N:41])([CH3:34])[CH3:33].C(=O)(O)[O-:53].[Na+]>CN(C=O)C>[CH:32]([N:35]([CH:49]([CH3:51])[CH3:50])[P:36]([O:37][CH2:38][CH2:39][C:40]#[N:41])[O:53][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)([CH3:34])[CH3:33]

참가 물질

6

반응물 4

HCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 516892Sodium BicarbonateHCID 131716339N-biotinylaminoethanolHCID 178458033HCID 178458033, 화합물

생성물 1

HCID 15085418N-biotinyl-aminoethyl 2-cyanoethyl N,N-diisopropylphosphoramidite

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 150 mg of N-biotinylaminoethanol (2a) 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 1.25 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 that formed was collected by suction filtration under argon, affording after drying at room temperature under vacuum 109 mg (43%) of a colorless solid.

후처리

  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

출처 및 근거

ORD 기록
ord-27e1cf4b3e724bb69da2d6e18c0549f7
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04908453

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