Trifluridine → HCID 14722799, compound

HRID 1655490Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1.[CH3:21][C:22]([CH3:41])(O[CH2:30][O:31][C:32]([CH3:40])([CH3:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(C)C(S(OS(C2C(C)=CC=CC=2)(=O)=O)(=O)=O)=CC=CC=1>O1CCOCC1>[CH3:21][C:22]([O:14][CH2:13][C@H:12]1[O:15][C@@H:8]([N:7]2[CH:16]=[C:3]([C:2]([F:1])([F:19])[F:20])[C:4](=[O:18])[NH:5][C:6]2=[O:17])[CH2:9][C@@H:10]1[OH:11])([CH3:41])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:40][C:32]([O:31][C@@H:30]1[C@@H:12]([CH2:10][OH:11])[O:15][C@@H:8]([N:7]2[CH:16]=[C:3]([C:2]([F:20])([F:1])[F:19])[C:4](=[O:18])[NH:5][C:6]2=[O:17])[CH2:9]1)([CH3:39])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1.00 Gram of 2'-deoxy-5-trifluoromethyluridine was dissolved in 15 ml of 1,4-dioxane. Thereto were added 2.50 g of bis-(α,α-dimethylbenzyloxy)methane and 38 mg of toluenesulfonic acid anhydride. They were heated to 60° C. and stirred for 3.5 hours. The reaction mixture was subjected to evaporation. The residue was subjected to silica gel column chromatography wherein a developing solvent of chloroform-methanol (20:1) was first used for preliminary separation and then a developing solvent of benzene-acetone (10:1) was used, to obtain 0.40 g (yield: 29.2%) of hygroscopic and amorphous 2'-deoxy-5'-O-(α,α-dimethylbenzyl)-5-trifluoromethyl uridine (compound 22) and 0.28 g (yield: 20.4%) of hygroscopic and amorphous 2'-deoxy-3'-O-(α,α-dimethylbenzyl)-5-trifluoromethyluridine (compound 23).

Workup

customThe reaction mixture was subjected to evaporation
customwas first used for preliminary separation

Sources & evidence

ORD record: ord-8007b013312049cfb19c6e8f0209774f
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05250673

Reaction notes

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