Methanol → HCID 21962929, compound

HRID 227461Notes

Reaction equation

HRID 227461 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[Cl:9][C:10]1[CH:11]=[C:12]([CH:36]=[CH:37][C:38]=1[Cl:39])[CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH:16]([CH2:20][NH:21][C:22](=[O:35])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH:25]=2)[CH2:15]1.CO>CC(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([CH:36]=[CH:37][C:38]=1[Cl:39])[CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH:16]([CH2:20][NH:21][C:22](=[O:35])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N:30]([CH3:1])[S:31]([CH3:34])(=[O:32])=[O:33])[CH:25]=2)[CH2:15]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodide3×HCID 11430Potassium Carbonate2×HCID 21962960HCID 21962960, compound

Product 1

HCID 21962929HCID 21962929, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (0.035 g) and iodomethane (0.015 ml) were added to a stirred solution of Example 139 (0.115 g) in acetone (1 ml), and stirring was continued at 22° C. for 72 h before a further portion of iodomethane (0.003 ml) was added. After stirring for a further 24 h, more iodomethane (0.003 ml) and potassium carbonate (0.007 g) were added, and the mixture stirred for a further 48 h. The mixture was applied in two equal portions to two ion exchange cartridges (2 g Isolute SCX, pre-conditioned with methanol). Elution with methanol (3 column volumes) followed by 10% 0.880 ammonia in methanol (2 column volumes), and evaporation of the first basic fraction from each elution in vacuo gave the title compound as a pale yellow gum (0.038 g).

Workup

  1. additionwas added
  2. stirringAfter stirring for a further 24 h
  3. stirringthe mixture stirred for a further 48 h
  4. washElution with methanol (3 column volumes)
  5. customfollowed by 10% 0.880 ammonia in methanol (2 column volumes), and evaporation of the first basic fraction from each elution in vacuo

Sources & evidence

ORD record
ord-76e83fa27ff84adc8c7cb6514f8c3cb5
Source dataset
uspto-grants-2009_07
Patent number
US07560548B2

Reaction notes

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