3-Furoic acid → HCID 54021445, compound

HRID 1089415Notes

Reaction equation

HRID 1089415 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.C(C1C=C(C(C)C)C=C(C(C)C)C=1S(Cl)(=O)=O)(C)C.[Si]([O:35][C@@H:36]1[C@H:40]([O:41][Si](C(C)(C)C)(C)C)[C@@H:39]([CH3:49])[O:38][C@H:37]1[N:50]1[CH:57]=[C:56]([F:58])[C:54]([NH2:55])=[N:53][C:51]1=[O:52])(C(C)(C)C)(C)C>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:58][C:56]1[C:54]([NH:55][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[O:8])=[N:53][C:51](=[O:52])[N:50]([CH:57]=1)[C@@H:37]1[O:38][C@H:39]([CH3:49])[C@@H:40]([OH:41])[C@H:36]1[OH:35]

Participants

6

Reactant 3

HCID 102683-Furoic acidHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 18641814HCID 18641814, compound

Product 1

HCID 54021445HCID 54021445, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

3-Furoic acid (0.355 g) and 2,4,6-triisopropyl benzene-sulfonyl chloride (0.96 g) were dissolved in dry pyridine (5 ml). The mixture was stirred for 1 hour. To the mixture were added 2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxy-5-fluorocytidine (1.0 g) obtained in Reference example (a) and 4-dimethylaminopyridine (0.80 g). After stirring of the mixture for 12 hours at room temperature. pyridine was evaporated under reduced pressure. The residue was then treated as in Example 48 to give 0.55 g of 5'-deoxy-5-fluoro-N4 -(3-furoyl)cytidine, mp 173°~174° C. (ethanol); MS 340 (MH+).

Workup

  1. stirringAfter stirring of the mixture for 12 hours at room temperature
  2. custompyridine was evaporated under reduced pressure
  3. additionThe residue was then treated as in Example 48

Sources & evidence

ORD record
ord-44efe5abbe0842ea9baa88cadaac71ad
Source dataset
uspto-grants-1990_10
Patent number
US04966891

Reaction notes

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