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

HRID 466106

Reaction equation

HRID 466106 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-54432c8d643d439397ff68f751c45744
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Linked notes

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