Hydroxide → 2'-deoxy-5-fluoro-3'-O-(4-methoxycarbonylbenzyl)uridine

HRID 466106

반응식

HRID 466106 반응식
[OH-].[CH3:2][O:3][C:4]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Br)=[CH:8][CH:7]=1)=[O:5].[F:14][C:15]1[C:16](=[O:49])[NH:17][C:18](=[O:48])[N:19]([CH:47]=1)[C@@H:20]1[O:46][C@H:24]([CH2:25][O:26]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:22]([OH:23])[CH2:21]1>O1CCOCC1>[F:14][C:15]1[C:16](=[O:49])[NH:17][C:18](=[O:48])[N:19]([CH:47]=1)[C@@H:20]1[O:46][C@H:24]([CH2:25][OH:26])[C@@H:22]([O:23][CH2:10][C:9]2[CH:12]=[CH:13][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:7][CH:8]=2)[CH2:21]1

참가 물질

5

반응물 3

HCID 961HydroxideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 108387042'-deoxy-5'-O-trityl-5-fluorouridine

생성물 1

HCID 140495822'-deoxy-5-fluoro-3'-O-(4-methoxycarbonylbenzyl)uridine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Pottasium hydroxide (4.30 g) and 1.70 g of 4-methoxycarbonylbenzyl bromide were added to a solution of 3.00 g of 2'-deoxy-5-fluoro-5'-O-trityluridine in 200 ml of dioxane. The mixture was stirred at room temperature for a day. The reaction mixture was concentrated under a reduced pressure. To the concentrate was added 200 ml of ethyl acetate for extraction. The extract was washed with water, dried over magnesium sulfate and concentrated. The concentrate was dissolved in 20 ml of a 80% aqueous solution of acetic acid.

후처리

  1. concentrationThe reaction mixture was concentrated under a reduced pressure
  2. additionTo the concentrate was added 200 ml of ethyl acetate
  3. extractionfor extraction
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved in 20 ml of a 80% aqueous solution of acetic acid

출처 및 근거

ORD 기록
ord-54432c8d643d439397ff68f751c45744
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155113

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