Hydrochloric Acid → 2-Chloroadenosine

HRID 917838

반응식

HRID 917838 반응식
C([C@@:4]1([OH:30])[C@:8](C(=O)C)([OH:9])[C@@H:7]([CH:13](C(=O)C)[OH:14])[O:6][C@H:5]1[N:18]1[C:28]2[N:27]=[C:25](N)[NH:24][C:22](Cl)(O)[C:21]=2[N:20]=[CH:19]1)(=O)C.[N:31]([O-])=O.[Na+].[ClH:35]>O.N>[Cl:35][C:25]1[N:24]=[C:22]([NH2:31])[C:21]2[N:20]=[CH:19][N:18]([C:28]=2[N:27]=1)[C@@H:5]1[O:6][C@H:7]([CH2:13][OH:14])[C@@H:8]([OH:9])[C@H:4]1[OH:30]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 178472536HCID 178472536, 화합물

생성물 1

HCID 89742-Chloroadenosine수율 60%

시약·촉매·용매 2

HCID 222Ammonia용매2회HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

100 g of 2',3',5'-triacetyl-6-chloroguanosine was dissolved in 400 ml of concentrated hydrochloric acid and, after the mixture was cooled to 0°C, a solution of 20 g of sodium nitrite dissolved in 50 ml of water was then added slowly to the mixture. The resulting mixture was allowed to react for 30 minutes, neutralized with concentrated aqueous ammonia and extracted with 2 l of methylene chloride. The extract was dried over anhydrous sodium sulfate and concentrated. The concentrate thus-obtained was dissolved in 300 ml of saturated methanolic ammonia and the mixture was allowed to react at a temperature of 100°C for 5 hours in a sealed tube. The reaction mixture was then concentrated to dryness and the residue was crystallized from water to obtain 42.3 g (60% yield) of 2-chloroadenosine. Recrystallization from water was repeated to obtain crystals having the following constant physical properties. Melting Point: 161° ~ 162°C (with decomposition)

후처리

  1. additionwas then added slowly to the mixture
  2. customto react for 30 minutes
  3. extractionextracted with 2 l of methylene chloride
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe concentrate thus-obtained
  7. customto react at a temperature of 100°C for 5 hours in a sealed tube
  8. concentrationThe reaction mixture was then concentrated to dryness
  9. customthe residue was crystallized from water

출처 및 근거

ORD 기록
ord-c57adab49dea4d91965af19d4b410f11
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03968102

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