Potassium Hydroxide → HCID 15124907, compound

HRID 981732Notes

Reaction equation

[F:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:35])[N:6]([CH:34]=1)[C@@H:7]1[O:33][C@H:11]([CH2:12][O:13]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:9]([OH:10])[CH2:8]1.[OH-].[K+].C[O:40][C:41]([C:43]1[O:49][C:46]([CH2:47]Cl)=[CH:45][CH:44]=1)=[O:42]>O1CCOCC1>[C:41]([C:43]1[O:49][C:46]([CH2:47][O:10][C@@H:9]2[C@@H:11]([CH2:12][OH:13])[O:33][C@@H:7]([N:6]3[CH:34]=[C:2]([F:1])[C:3](=[O:36])[NH:4][C:5]3=[O:35])[CH2:8]2)=[CH:45][CH:44]=1)([OH:42])=[O:40]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5.00 g of 2'-deoxy-5-fluoro-5'-O-trityluridine in 100 ml of dioxane were added 5.74 g of fine powder of potassium hydroxide and 2.67 g of 5-methoxycarbonylfurfuryl chloride, and the mixture was stirred at temperature of 80° C. for 2.5 hours. The reaction mixture was concentrated and the residue was dissolved in 100 ml of water. The reaction mixture was adjusted to a pH of 4 with one normal hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried and concentrated To the residue was added 100 ml of 80% acetic acid The mixture was left to stand at a temperature of 80° C. for one hour. The solvent was distilled off and the residue was washed with ethyl acetate and methanol, giving 2.53 g (67%) of 3'-O-(5carboxyfurfuryl)-2'-deoxy-5-fluorouridine.

Workup

concentrationThe reaction mixture was concentrated
dissolutionthe residue was dissolved in 100 ml of water
extractionextracted with ethyl acetate
customThe organic layer was dried
concentrationconcentrated To the residue
additionwas added 100 ml of 80% acetic acid The mixture
waitwas left
waitto stand at a temperature of 80° C. for one hour
distillationThe solvent was distilled off
washthe residue was washed with ethyl acetate and methanol

Sources & evidence

ORD record: ord-a335501e1ffe40a69ca2d75e2a269ed5
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04992534

Reaction notes

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