Dideoxycytidine → Diisopropylaminomethylene 2',3'-dideoxycytidine

HRID 729053

반응식

HRID 729053 반응식
[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]

참가 물질

4

반응물 2

HCID 24066DideoxycytidineHCID 13161384Diisopropylformamide Dimethylacetal (>90%)

생성물 1

HCID 131717010Diisopropylaminomethylene 2',3'-dideoxycytidine수율 79.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fa786e27cfb34f2f97e82278b77890f2
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05051498

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