Carbon tetrabromide → 5'-Azido-2',5'-dideoxy-5-n-propyluridine

HRID 232387

反応式

HRID 232387 の反応式
[CH2:1]([C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14]O)[C@@H:11]([OH:12])[CH2:10]1)[CH2:2][CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:39]=[N+:40]=[N-:41].[Na+].C(Br)(Br)(Br)Br>CN(C)C=O.CO>[N:39]([CH2:14][C@H:13]1[O:16][C@@H:9]([N:8]2[CH:17]=[C:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:19])[NH:6][C:7]2=[O:18])[CH2:10][C@@H:11]1[OH:12])=[N+:40]=[N-:41]

参加物

7

反応物 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 1601555-Propyl-2'-deoxyuridine

生成物 1

HCID 539281315'-Azido-2',5'-dideoxy-5-n-propyluridine収率 65.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

0.57 g of 2'-deoxy-5-n-propyluridine, 0.6 g of triphenylphosphine and 0.69 g of sodium azide were stirred in 20 ml of dry dimethylformamide. 0.77 g of carbon tetrabromide was added over a period of 5 minutes. The mixture was stirred at room temperature for 72 hours, 20 ml of methanol were added and the mixture was stirred for a further 0.5 hour. The mixture was evaporated and the residue was stirred with a mixture of 25 ml of dichloromethane/methanol (8:2). An insoluble solid was removed by filtration and the filtrate was chromatographed on 200 g of silica gel in the same solvent mixture to give 0.41 g of 5'-azido-2',5'-dideoxy-5-n-propyluridine of melting point 177°-179° C. (decomposition).

後処理

  1. stirringthe mixture was stirred for a further 0.5 hour
  2. customThe mixture was evaporated
  3. stirringthe residue was stirred with a mixture of 25 ml of dichloromethane/methanol (8:2)
  4. customAn insoluble solid was removed by filtration
  5. customthe filtrate was chromatographed on 200 g of silica gel in the same solvent mixture

出典と根拠

ORDレコード
ord-0a2e7aed9a5047d9bc8b2b95103a864d
出典データセット
uspto-grants-1989_07
特許番号
US04851519

関連ノート

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