5'-Amino-2',5'-dideoxy-5-ethyluridine → 2',5'-dideoxy-5-ethyl-5'-[2(RS)-(2,4-dichlorophenoxy)propylamino]uridine

HRID 1031864

反応式

HRID 1031864 の反応式
[NH2:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:15]=[C:14]([CH2:16][CH3:17])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:18].C([BH3-])#N.[Na+].[Cl:23][C:24]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:25]=1[O:26][CH:27]([CH3:30])[CH:28]=O>CO.O>[CH2:16]([C:14]1[C:12](=[O:13])[NH:11][C:9](=[O:10])[N:8]([CH:15]=1)[C@@H:6]1[O:7][C@H:3]([CH2:2][NH:1][CH2:30][CH:27]([O:26][C:25]2[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:24]=2[Cl:23])[CH3:28])[C@@H:4]([OH:18])[CH2:5]1)[CH3:17]

参加物

6

反応物 3

HCID 4518285'-Amino-2',5'-dideoxy-5-ethyluridineHCID 5003444Sodium cyanoborohydrideHCID 221663592-(2,4-Dichlorophenoxy)propanal

生成物 1

HCID 186361762',5'-dideoxy-5-ethyl-5'-[2(RS)-(2,4-dichlorophenoxy)propylamino]uridine収率 32.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution, cooled in ice, of 0.45 g of 5'-amino-2',5'-dideoxy-5-ethyluridine in 28 ml of methanol and 9 ml of water were added 0.17 g of sodium cyanoborohydride followed by 0.5 g of 2-(2,4-dichlorophenoxy)propionaldehyde. The mixture was allowed to warm to room temperature and was then stirred at room temperature for 3 days. The solution was concentrated in order to remove methanol, diluted with 20 ml of water and extracted three times with 15 ml of methylene chloride. The combined extracts were dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using methanol/methylene chloride (1:12) for the elution. There was obtained 0.26 g of 2',5'-dideoxy-5-ethyl-5'-[2(RS)-(2,4-dichlorophenoxy)-propylamino]uridine, mp 51°-61° C.

後処理

  1. concentrationThe solution was concentrated in order
  2. customto remove methanol
  3. additiondiluted with 20 ml of water
  4. extractionextracted three times with 15 ml of methylene chloride
  5. dry with materialThe combined extracts were dried over sodium sulphate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washfor the elution

出典と根拠

ORDレコード
ord-e642e6b0bb014088b8fa478578be2c08
出典データセット
uspto-grants-1990_09
特許番号
US04956346

関連ノート

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