Ammonia → N4-(3,5,5-trimethyl-1-hexanoyl)-2'-deoxycytidine

HRID 84065

반응식

HRID 84065 반응식
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.C[Si](Cl)(C)C.[CH3:22][CH:23]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:24][C:25](Cl)=[O:26].N>N1C=CC=CC=1>[CH3:22][CH:23]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:24][C:25]([NH:14][C:13]1[CH:15]=[CH:16][N:9]([C@@H:1]2[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]2)[C:10](=[O:11])[N:12]=1)=[O:26]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 6397ChlorotrimethylsilaneHCID 13711DeoxycytidineHCID 1619293,5,5-Trimethylhexanoyl chloride

생성물 1

HCID 86698897N4-(3,5,5-trimethyl-1-hexanoyl)-2'-deoxycytidine수율 127.9%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Suspending 2′-Deoxycytidine (2.3 g, 10.0 mmol) in dry pyridine, followed by concentration under reduced pressure was repeated 3 times to perform dehydrative azeotropic distillation, the concentrate was suspended again in dry pyridine (60 ml), and trimethylsilyl chloride (6.4 ml, 50 mmol) was added dropwise over 5 min. To the reaction mixture was added 3,5,5-trimethyl-1-hexanoyl chloride (9.5 ml, 50.0 mmol) over 5 min. After completion of the reaction, under ice-cooling, aqueous ammonia (25 ml) was added and the mixture was reacted for 20 min. The reaction mixture was concentrated under reduced pressure. Water (150 ml) was added to the concentrate, and the mixture was extracted 3 times with ethyl acetate (100 ml). The organic layer was concentrated and the obtained oil was purified by silica gel column chromatography to give the title compound (4.7 g).

후처리

  1. concentrationfollowed by concentration under reduced pressure
  2. distillationazeotropic distillation
  3. customAfter completion of the reaction
  4. temperatureunder ice-cooling
  5. customthe mixture was reacted for 20 min
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. additionWater (150 ml) was added to the concentrate
  8. extractionthe mixture was extracted 3 times with ethyl acetate (100 ml)
  9. concentrationThe organic layer was concentrated
  10. customthe obtained oil was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e1342269c6c64ced828ebd7673f082dc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846885B2

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