Dideoxycytidine → Diisopropylaminomethylene 2',3'-dideoxycytidine

HRID 1419455

反应方程式

HRID 1419455 反应方程式
[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]

参与物

4

反应物 2

HCID 24066DideoxycytidineHCID 13161384Diisopropylformamide Dimethylacetal (>90%)

产物 1

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

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

In a typical example of such procedure, previously dried 2', 3'-dideoxycytidine (153 mg, 0.724 mmoles) which was previously 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 product is stirred overnight and thereafter solvent and excess reagent are removed by rotary evaporation. The syrupy residue remaining is crystallized from ethanolether to give pale lemon-colored crystals (185 mg, 79%) of diisopropylaminomethylene 2', 3'-dideoxycytidine.

后处理

  1. customsolvent and excess reagent are removed by rotary evaporation
  2. customThe syrupy residue remaining is crystallized from ethanolether

来源与证据

ORD记录
ord-6996bb5d200c4eb2b91a51600ce8e971
来源数据集
uspto-grants-1999_03
专利号
US05886162

关联笔记

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