Benzyl mercaptan → HCID 54185340、化合物

HRID 1638981ノート

反応式

HRID 1638981 の反応式
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]([C:13]1[C:14](=[O:38])[NH:15][C:16](=[O:37])[N:17]([CH:36]=1)[C@@H:18]1[O:35][C@H:22]([CH2:23]OS(C2C=CC(C)=CC=2)(=O)=O)[C@@H:20]([OH:21])[CH2:19]1)[CH3:12]>CN(C)C=O>[CH2:1]([S:8][CH2:23][C@H:22]1[O:35][C@@H:18]([N:17]2[CH:36]=[C:13]([CH2:11][CH3:12])[C:14](=[O:38])[NH:15][C:16]2=[O:37])[CH2:19][C@@H:20]1[OH:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 5280128HCID 5280128、化合物

生成物 1

HCID 54185340HCID 54185340、化合物収率 100.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
100 °C

実験手順

A solution of 0.5 g of benzyl mercaptan in 10 ml of dry dimethylformamide was treated with 60 mg of a 80% dispersion of sodium hydride in mineral oil. After the effervescence had ceased a solution of 1.64 g of 2'-deoxy-5-ethyl-5'-O-(p-toluenesulphonyl)uridine in 20 ml of dry dimethylformamide was added. The mixture was stirred and heated at 100° C. under a nitrogen gas atmosphere. The course of the reaction was followed by thin layer chromatography. After 4 hours the mixture was evaporated to give an oily residue. This was purified by flash column chromatography on silica gel using methanol/dichloromethane (1:9) for the elution. The fractions containing the product were combined and evaporated to yield an oil which solidified and was recrystallized from diethyl ether to give 1.46 g of 5'-benzylthio-2',5'-dideoxy-5-ethyluridine, mp 149°-151° C.

後処理

  1. additionwas added
  2. customAfter 4 hours the mixture was evaporated
  3. customto give an oily residue
  4. customThis was purified by flash column chromatography on silica gel
  5. washfor the elution
  6. additionThe fractions containing the product
  7. customevaporated
  8. customto yield an oil which
  9. customwas recrystallized from diethyl ether

出典と根拠

ORDレコード
ord-d0f60e6bd21343b28405df8bc23919bd
出典データセット
uspto-grants-1989_11
特許番号
US04882316

反応ノート

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