Cytidine → HCID 54146375, 화합물

HRID 328557

반응식

HRID 328557 반응식
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[H][H]>[Rh].O>[NH2:15][CH:14]1[CH2:16][CH2:17][N:10]([C@@H:1]2[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]2[OH:3])[C:11](=[O:12])[NH:13]1

참가 물질

5

반응물 2

HCID 6175CytidineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 54146375HCID 54146375, 화합물

시약·촉매·용매 2

HCID 23948Rhodium촉매HCID 962Water용매

실험 절차

A solution of 17.5 g. (72 millimoles) of cytidine in 540 ml. of water was hydrogenated in a Parr hydrogenator at 30 psi pressure, in the presence of 3.6 g. of 5% rhodium on alumina catalyst. Hydrogen uptake overnight (18-19 hours) was approximately 2 molar equivalents. The solution (pH 10.5) was filtered through a bed of Celite (diatomaceous earth) filter and lyophilized to yield 4-amino-1-β-D-ribofuranosyl-tetrahydro-2(1H)-pyrimidinone as a white amorphous solid. When examined by nuclear magnetic resonance the solid showed a doublet at 5.95 ppm. (anomeric proton); multiplet at 4.50 ppm. ##STR12## multiplets at 3.45 ppm. (--CH2N=) and 2.00 ppm. (C--CH2 --C) and a small amount of absorption at 2.75 ppm. ##STR13## Upon acidification, the 4.50 ppm. multiplet moved downfield to 5.08 ppm. ##STR14## and part of the 2.00 ppm. multiplet moved slightly downfield to 2.2 ppm. Peak locations are referred to the peak for sodium-2,2-dimethyl-2-silapentane-5-sulfonate (SDSS) as internal standard. Held in aqueous solution at pH 5.5 to 6 overnight, the solid was converted to and gave the analytical characteristics of 4-hydroxy-1-β-D-ribofuranosyl-tetrahydro-2(1H)-pyrimidinone.

후처리

  1. filtrationThe solution (pH 10.5) was filtered through a bed of Celite (diatomaceous earth)
  2. filtrationfilter

출처 및 근거

ORD 기록
ord-9fd2fac748044bb686ffd6d512c322f2
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04017606

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