HCID 10578070, compound → HCID 10253865, compound

HRID 1709023Notes

Reaction equation

HRID 1709023 reaction equation
C(OC([NH:8][CH2:9][C:10]([O:12][CH2:13][C@H:14]1[O:18][C@@H:17]([N:19]2[CH:26]=[C:25]([F:27])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:16][C@@H:15]1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)=[O:11])=O)(C)(C)C>Cl.O1CCOCC1>[ClH:36].[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][O:28][C@@H:15]2[C@@H:14]([CH2:13][O:12][C:10](=[O:11])[CH2:9][NH2:8])[O:18][C@@H:17]([N:19]3[CH:26]=[C:25]([F:27])[C:23](=[O:24])[NH:22][C:20]3=[O:21])[CH2:16]2)=[CH:31][CH:32]=1

Participants

3

Reactant 1

HCID 10578070HCID 10578070, compound

Product 1

HCID 10253865HCID 10253865, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

In 3 ml of 4N-HCl-dioxane was dissolved 0.88 g of 5'--O--[N-(t-butoxycarbonyl)glycyl]-3'-O-(4-chlorobenzyl)- 2'-deoxy-5-fluorouridine obtained in Example 8 (A), and the solution was left to stand for 30 minutes at room temperature. The solvent was distilled off and the residue was placed on silica gel column and eluted with 4-6% methanol-chloroform, giving 0.36 g (45%) of 3'-O-(4-chlorobenzyl)-2'-deoxy-5-fluoro-5'-O-glycyluridine hydrochloride.

Workup

  1. waitthe solution was left
  2. distillationThe solvent was distilled off
  3. washeluted with 4-6% methanol-chloroform

Sources & evidence

ORD record
ord-a565ebccaee243a480c46592fc9229a1
Source dataset
uspto-grants-1990_08
Patent number
US04946951

Reaction notes

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