Dideoxycytidine → Diisopropylaminomethylene 2',3'-dideoxycytidine

HRID 1419455

반응식

HRID 1419455 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 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.

후처리

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

출처 및 근거

ORD 기록
ord-6996bb5d200c4eb2b91a51600ce8e971
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886162

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