2',3'-Didehydro-2',3'-dideoxyuridine → 2',3'-Dideoxyuridine

HRID 381216

반응식

HRID 381216 반응식
[C@@H:1]1([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[O:7][C@H:4]([CH2:5][OH:6])[CH:3]=[CH:2]1.[H][H]>CO.[Pd]>[C@@H:1]1([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[O:7][C@H:4]([CH2:5][OH:6])[CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 651592',3'-Didehydro-2',3'-dideoxyuridineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 651612',3'-Dideoxyuridine수율 97.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A solution of 2′,3′-dideoxy-2′,3′-didehydrouridine (1.0 g, 4.8 mmol) in methanol (10 ml) containing a catalyst (wet 5% palladium on carbon) (400 mg) was stirred in an atmosphere of hydrogen for 1 h. The catalyst was removed by filtration and the filtrate was concentrated. The residue was chromatographed on silica gel (CHCl3/MeOH=5/1) to give 2′,3′-dideoxyuridine (0.99 g, 97% yield): Mp 121.2-121.7° C.; λmax(MeOH) 262 nm (ε 10560), λmin(MeOH) 232 nm (ε 3810); 1H-NMR (Me2SO-d6) δ 1.74-2.00 (m, 3H), 2.20-2.35 (m, 1H), 3.49-3.55 (m, 1H), 3.64-3.69 (m, 1H), 4.00-4.03 (brs, 1H), 5.03 (s, 1H), 5.58 (d, 1H, J=8.06 Hz), 5.95 (m, 1H), 7.94 (d, 1H, J=8.06 Hz), 11.25 (brs, 1H); Fast atom bombardment mass spectrum m/z 213 (MH+). Anal. Calcd for C9H12N2O4: C, 50.94;H, 5.70; N, 13.20. Found: C, 50.95;H, 5.71; N, 13.20.

후처리

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was chromatographed on silica gel (CHCl3/MeOH=5/1)

출처 및 근거

ORD 기록
ord-cb98a5aadfd548099b1fa021db6bc9fb
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306647B1

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