Ammonia → N2 (3-methoxyphenylacetyl)-2'-deoxyguanosine

HRID 54639

반응식

HRID 54639 반응식
[C@@H:1]1([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.C[Si](Cl)(C)C.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34](Cl)=[O:35])[CH:30]=[CH:31][CH:32]=1.[NH3:37]>N1C=CC=CC=1.O>[N:37]#[N:9].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34]([C@@:1]2([N:9]3[C:19]4[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=4[N:11]=[CH:10]3)[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]2)=[O:35])[CH:30]=[CH:31][CH:32]=1

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 6397ChlorotrimethylsilaneHCID 27332463-Methoxyphenylacetyl chlorideHCID 135398592Deoxyguanosine

생성물 1

HCID 136381143N2 (3-methoxyphenylacetyl)-2'-deoxyguanosine수율 75%

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

To dry 2'-deoxyguanosine (1) (14.2 g, 50 mmoles) in 300 ml of dry pyridine at 0° C. was added trimethylsilyl chloride (33 ml, 250 mmoles) and the mixture stirred at 0° C. for 1 hour. 3-Methoxyphenylacetyl chloride (40 ml, 250 mmoles) was added and the solution maintained at room temperature for 15 hours. The reaction mixture was then cooled in an ice bath and 50 ml of cold water was added. After 30 minutes, 50 ml of 29% aqueous ammonia was added and the mixture stirred for 30 minutes. The solution was then evaporated to near dryness and the residue dissolved in 400 ml water and 400 ml methylene chloride in a separating funnel. The product crystallized out of the aqueous solution upon extraction with CH2Cl2 was filtered off, washed with CH2Cl2 (3×50 ml) and ether (3×50 ml) and air dried to yield 15.56 g (75%) of N2 -(3-methoxyphenylacetyl)-2'-deoxyguanosine (2b), as confirmed by spectroscopic and elemental analysis.

후처리

  1. temperaturethe solution maintained at room temperature for 15 hours
  2. temperatureThe reaction mixture was then cooled in an ice bath
  3. waitAfter 30 minutes
  4. stirringthe mixture stirred for 30 minutes
  5. customThe solution was then evaporated
  6. dissolutionthe residue dissolved in 400 ml water
  7. customThe product crystallized out of the aqueous solution upon extraction with CH2Cl2
  8. filtrationwas filtered off
  9. washwashed with CH2Cl2 (3×50 ml) and ether (3×50 ml) and air
  10. customdried

출처 및 근거

ORD 기록
ord-2beef6d9805c485f9593c5e6dac7e3f9
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623068

연결된 노트

불러오는 중…