Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 14997846, compound

HRID 728618Notes

Reaction equation

HRID 728618 reaction equation
[CH2:1]([CH:4]([CH2:48][CH2:49][CH3:50])[C:5]([NH:7][CH2:8][C:9]([O:11][C@@H:12]1[C@@H:16]([CH2:17][O:18][C:19](=[O:31])[CH2:20][NH:21][C:22](=[O:30])[CH:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[O:15][C@@H:14]([N:32]2[CH:39]=[C:38]([F:40])[C:36](=[O:37])[NH:35][C:33]2=[O:34])[C@@H:13]1[O:41]C1CCCCO1)=[O:10])=[O:6])[CH2:2][CH3:3].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[CH2:1]([CH:4]([CH2:48][CH2:49][CH3:50])[C:5]([NH:7][CH2:8][C:9]([O:11][C@@H:12]1[C@@H:16]([CH2:17][O:18][C:19](=[O:31])[CH2:20][NH:21][C:22](=[O:30])[CH:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[O:15][C@@H:14]([N:32]2[CH:39]=[C:38]([F:40])[C:36](=[O:37])[NH:35][C:33]2=[O:34])[C@@H:13]1[OH:41])=[O:10])=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 14997845HCID 14997845, compound

Product 1

HCID 14997846HCID 14997846, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 6 ml of ethanol was dissolved 0.5 g of 3',5'-bis-O-[N-(2-n-propyl-n-pentanoyl)glycyl]-2'-O-(2-tetrahydropyranyl)-5-fluorouridine, and after adding 18 mg of pyridinium p-toluenesulfonate at room temperature under stirring, the mixtuer was stirred at 55° C. for 3.5 hours. The residue obtained by condensing the reaction mixture under reduced pressure was applied to silica gel column chromatography to give 0.34 g (Yield: 77%) of the title compound.

Workup

  1. stirringthe mixtuer was stirred at 55° C. for 3.5 hours
  2. customThe residue obtained by condensing the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-06fd922d4c2d470db95202b43c84a843
Source dataset
uspto-grants-1991_09
Patent number
US05049551

Reaction notes

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