5'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]uridine → HCID 178485725, 화합물

HRID 1665823

반응식

HRID 1665823 반응식
[CH3:1][O:2][C:3]1[CH:46]=[CH:45][C:6]([C:7]([O:22][CH2:23][C@H:24]2[O:28][C@@H:27]([N:29]3[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]3=[O:31])[C@H:26]([O:37][CH2:38][CH2:39][C:40](=[O:43])[NH:41][CH3:42])[C@@H:25]2[OH:44])([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.C(N(C(C)C)[P:51]([N:58]([CH:62]([CH3:64])[CH3:63])[CH:59]([CH3:61])[CH3:60])[O:52]OCCC#N)(C)C.[NH:68]1[C-:72]=NN=N1.[CH:73]([NH2+]C(C)C)(C)[CH3:74]>C(#N)C>[C:72]([CH2:73][CH2:74][PH:51]([O:44][C@@H:25]1[C@@H:24]([CH2:23][O:22][C:7]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:6]2[CH:45]=[CH:46][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:28][C@@H:27]([N:29]2[CH:36]=[CH:35][C:33](=[O:34])[NH:32][C:30]2=[O:31])[C@@H:26]1[O:37][CH2:38][CH2:39][C:40](=[O:43])[NH:41][CH3:42])([N:58]([CH:59]([CH3:60])[CH3:61])[CH:62]([CH3:63])[CH3:64])[OH:52])#[N:68]

참가 물질

5

반응물 3

HCID 532538595'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]uridineHCID 866383062-cyanoethoxy N,N,N',N'-tetraisopropylphosphorodiamiditeHCID 178458033HCID 178458033, 화합물

생성물 1

HCID 178485725HCID 178485725, 화합물수율 78%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

The compound (490 mg, 0.77 mmol) prepared in Example 8 was dissolved in dried acetonitrile (2 mL), and 2-cyanoethoxy N,N,N′,N′-tetraisopropylphosphorodiamidite (358 mg, 1.19 mmol) dissolved in dried acetonitrile (2 mL) was added thereto. To the mixture was further added diisopropylammonium 1H-tetrazolide (101 mg, 0.59 mmol), followed by stirring at room temperature for 8 hours. The reaction was terminated by adding water thereto, and dilution with ethyl acetate was carried out. The organic layer was washed with saturated brine three times and a saturated sodium hydrogen carbonate aqueous solution three times. The organic layer was dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography eluting with chloroform:methanol (99:1, v/v) containing 0.5% triethylamine to give the title compound (384 mg, 66%).

후처리

  1. additionwas added
  2. customThe reaction was terminated
  3. additionby adding water
  4. washThe organic layer was washed with saturated brine three times
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washeluting with chloroform:methanol (99:1
  9. additionv/v) containing 0.5% triethylamine

출처 및 근거

ORD 기록
ord-4a1b9da55fb0403e8c1380fecb14414f
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039611B2

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