Dideoxycytidine → Diisopropylaminomethylene 2',3'-dideoxycytidine

HRID 729053

反応式

HRID 729053 の反応式
[C@@H:1]1([N:8]2[CH:15]=[CH:14][C:12]([NH2:13])=[N:11][C:9]2=[O:10])[O:7][C@H:4]([CH2:5][OH:6])[CH2:3][CH2:2]1.CO[CH:18](OC)[N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH:20]([N:19]([CH:18]=[C:2]1[CH2:3][C@@H:4]([CH2:5][OH:6])[O:7][C@H:1]1[N:8]1[CH:15]=[CH:14][C:12]([NH2:13])=[N:11][C:9]1=[O:10])[CH:23]([CH3:25])[CH3:24])([CH3:22])[CH3:21]

参加物

4

反応物 2

HCID 24066DideoxycytidineHCID 13161384Diisopropylformamide Dimethylacetal (>90%)

生成物 1

HCID 131717010Diisopropylaminomethylene 2',3'-dideoxycytidine収率 79.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In a typical reaction--previously dried 2',3'-dideoxycytidine (153 mg, 0.724 mmoles) prepared by the literature procedures described above is treated with diisopropylformamide dimethylacetal (1.27 g, 7.24 mmoles) in anhydrous DMF (2 mL) under an argon atmosphere. The contents are stirred overnight and then the solvent and excess reagent are removed by rotary evaporation. The syrupy residue remaining is crystallized from ethanol-ether to give pale lemon-colored crystals (185 mg, 79%) of diisopropylaminomethylene 2',3'-dideoxycytidine.

後処理

  1. customIn a typical reaction
  2. customthe solvent and excess reagent are removed by rotary evaporation
  3. customThe syrupy residue remaining is crystallized from ethanol-ether

出典と根拠

ORDレコード
ord-fa786e27cfb34f2f97e82278b77890f2
出典データセット
uspto-grants-1991_09
特許番号
US05051498

関連ノート

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