Uridine, 2',3'-dideoxy-5-ethyl-3'-iodo- → 5-Et-ddU

HRID 232360노트

반응식

HRID 232360 반응식
[CH2:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:10](I)[CH2:9]1)[CH3:2]>N.O.[Pd]>[CH2:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:14][C@H:11]([CH2:12][OH:13])[CH2:10][CH2:9]1)[CH3:2]

참가 물질

5

반응물 1

HCID 451824Uridine, 2',3'-dideoxy-5-ethyl-3'-iodo-

생성물 1

HCID 4514525-Et-ddU수율 71.3%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 222Ammonia용매HCID 962Water용매

실험 절차

A solution of 2.50 g of 2',3'-dideoxy-5-ethyl-3'-iodouridine in a mixture of 90 ml of ethanolic ammonia and 17 ml of water was hydrogenated over 5% palladium on barium sulfate catalyst at room temperature and under atmospheric pressure for 3 hours. The mixture was filtered and the filtrate was evaporated. The residue was extracted twice with 250 ml of hot ethyl acetate each time and the combined ethyl acetate extracts were evaporated. The residue was chromatographed on a short column of silica gel using ethyl acetate for the elution and the product was crystallized from a mixture of ethyl acetate and hexane to give 1.17 g of 2',3'-dideoxy-5-ethyluridine in the form of a white solid of melting point 109°-113° C.

후처리

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. extractionThe residue was extracted twice with 250 ml of hot ethyl acetate each time
  4. customthe combined ethyl acetate extracts were evaporated
  5. customThe residue was chromatographed on a short column of silica gel
  6. washfor the elution
  7. customthe product was crystallized from a mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-242e581e95754b6f8fb4fa6b1829b13a
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851519

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