Acetic Acid → HCID 67177835, compound

HRID 1516777Notes

Reaction equation

[Cl:1]Cl.[Cl:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:11]([F:16])[CH2:10]1.[C:20]([OH:23])(=[O:22])[CH3:21]>>[Cl:3][C:4]1([Cl:1])[CH:17]([O:22][C:20](=[O:23])[CH3:21])[N:8]([C@@H:9]2[O:15][C@H:12]([CH2:13][OH:14])[C@@H:11]([F:16])[CH2:10]2)[C:7](=[O:18])[NH:6][C:5]1=[O:19]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 24526Chlorine

HCID 451480Raluridine

Product 1

HCID 67177835HCID 67177835, compound

Procedure

Chlorine gas was bubbled slowly into a suspension of 5-chloro-3′-fluoro-2′,3′-dideoxyuridine (75 mg, 0.28 mmol) in glacial acetic acid (5 ml) at 25° C. with stirring until the light yellow-green color of the resulting solution persisted. The reaction was allowed to proceed for 30 min. at 25° C., prior to evaporation. Purification of the residue obtained by PTLC using ethylacetate:hexanes (3:7, v/v) as development solvent afforded diastereomer (6S)-5,5-dichloro-O6-5′-cyclo-5,6-dihydro-3′-fluoro-2′,3′-dideoxyuridine (R-31) and one diastereomer of 5,5-dichloro-6-acetoxy-5,6-dihydro-3′-fluoro-2′,3′-dideoxyuridine.

Workup

customto evaporation
customPurification of the residue
customobtained by PTLC

Sources & evidence

ORD record: ord-ec8667c06bea44d894c5390295e7b398
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227594B2

Reaction notes

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