Hydrogen Sulfide → 2-Thioadenosine

HRID 917839

반응식

HRID 917839 반응식
Cl[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[Na].[SH2:22]>CN(C)C=O.O.C(O)(=O)C>[CH:7]1[N:8]([C@@H:9]2[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[C:18]2[C:5](=[C:4]([NH2:20])[NH:3][C:2]([N:19]=2)=[S:22])[N:6]=1

참가 물질

7

반응물 3

HCID 402Hydrogen SulfideHCID 89742-ChloroadenosineHCID 5360545Sodium

생성물 1

HCID 64519652-Thioadenosine수율 100%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

2.0 g of 2-chloroadenosine was dissolved in a solution of 20 ml of anhydrous hydrogen sulfide and 1.5 g of sodium metal in 80 ml of dimethylformamide, and the mixture was allowed to react at a temperature of 80°C for 5 hours under anhydrous conditions. The reaction mixture was then diluted with 80 ml of water and neutralized with acetic acid followed by concentration. The resulting concentrate was dissolved in 75 ml of a mixture of n-butanol and water (2:1 by volume), and 25 ml of acetic acid was added to the solution. After allowing the mixture to cool, the precipitated crystals were filtered to obtain 21 g (100% yield) of crude 2-thioadenosine. The product thus-obtained was dissolved in dilute aqueous ammonia and adjusted to a pH of 4 with acetic acid to obtain pure 2-thioadenosine having a melting point of 196° ~ 199°C (with decomposition).

후처리

  1. customto react at a temperature of 80°C for 5 hours under anhydrous conditions
  2. concentrationfollowed by concentration
  3. concentrationThe resulting concentrate
  4. dissolutionwas dissolved in 75 ml of a mixture of n-butanol and water (2:1 by volume), and 25 ml of acetic acid
  5. additionwas added to the solution
  6. temperatureto cool
  7. filtrationthe precipitated crystals were filtered

출처 및 근거

ORD 기록
ord-2c8431e780274999a5c7c6c810700adf
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03968102

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