Sodium periodate → HCID 70169858, compound

HRID 279049Notes

Reaction equation

HRID 279049 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][S:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:30][C@H:29]([CH2:31][NH:32][C:33](=[O:35])[CH3:34])[O:28][C:27]4=[O:36])=[CH:22][CH:21]=3)=[O:19])=[CH:16][N:17]=2)[CH:14]=1>O.CO>[CH3:7][S:8]([C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH2:30][C@H:29]([CH2:31][NH:32][C:33](=[O:35])[CH3:34])[O:28][C:27]4=[O:36])=[CH:24][CH:25]=3)=[O:19])=[CH:16][N:17]=2)[CH:14]=1)=[O:2]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 57194150HCID 57194150, compound

Product 1

HCID 70169858HCID 70169858, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium periodate (0.067 g. 0.313 mM) in water (2.5 ml) was added to a stirred suspension of the title product from Example 37 (0.12 g. 0.283 mM) in MeOH (10 ml) and the mixture heated at gentle reflux for 3 hours. The mixture was filtered hot and allowed to cool. The solid which precipitated was filtered, washed with water and ether and purified by chromatography on a BondElut silica column with gradient elution increasing in polarity from dichloromethane to 10% MeOH/dichloromethane to give the title compound (0.07 g). MS: 441 (MH+); NMR 1.83 (3H, s); 2.9 (3H, s); 3.45 (2H, t); 3.83 (1H, m); 4.2 (1H, t); 4.75 (1H, m); 7.75 (2H, d) 7.9 (1H, m); 7.96 (2H; d); 8.05 (1H, d); 8.24 (1H, t); 8.36 (1H, s); 9.83 (1H, s).

Workup

  1. temperaturethe mixture heated
  2. temperatureat gentle reflux for 3 hours
  3. filtrationThe mixture was filtered hot
  4. temperatureto cool
  5. customThe solid which precipitated
  6. filtrationwas filtered
  7. washwashed with water and ether
  8. custompurified by chromatography on a BondElut silica column with gradient elution
  9. temperatureincreasing in polarity from dichloromethane to 10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-7ab70f96b5a649d28df266a08096d3ef
Source dataset
uspto-grants-2002_03
Patent number
US06362191B1

Reaction notes

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