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Methyl iodide → HCID 69907754, compound

HRID 618133
Notes
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Reaction equation

HRID 618133 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9](/[CH:14]=[C:15](\[S:30][CH2:31][CH:32]([OH:35])[CH2:33][OH:34])/[C:16]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)=[O:17])=[CH:10][NH:11]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:36]I.[H-].[Na+]>CN(C)C=O.O1CCCC1>[C:1]([NH:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9](/[CH:14]=[C:15](\[S:30][CH2:31][CH:32]([OH:35])[CH2:33][OH:34])/[C:16]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)=[O:17])=[CH:10][N:11]2[CH3:36])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69907738HCID 69907738, compound

Product 1

HCID 69907754HCID 69907754, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

Compound 125 (300.0 mg) obtained in Example 125 was dissolved in a mixed solvent of N,N-dimethylformamide and tetrahydrofuran (1:1), and methyl iodide (93.6 mg) and then sodium hydride (26.4 mg, 60% mineral oil dispersion) were added thereto, followed by stirring for 1.5 hours. The reaction solution was subjected to partitioning between chloroform and water, and the organic layer was successively washed with water and a saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crude crystals were washed with chloroform and recrystallized from a mixed solvent of ethanol, N,N-dimethylformamide, and water to give Compound 126 (249.7 mg).

Workup

  1. customto partitioning between chloroform and water
  2. washthe organic layer was successively washed with water
  3. dry with materiala saturated saline, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained crude crystals
  6. washwere washed with chloroform
  7. customrecrystallized from a mixed solvent of ethanol, N,N-dimethylformamide, and water

Sources & evidence

ORD record
ord-d110662bdc174f148fdae9c736e1887c
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05952355

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes