Methyl iodide → HCID 68518335, compound

HRID 748930Notes

Reaction equation

HRID 748930 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH3:26])[CH:21]=3)[C:16]=2[O:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[CH:30][CH:29]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:46]>CN(C)C=O>[C:1]([N:5]([CH3:46])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH3:26])[CH:21]=3)[C:16]=2[O:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]3[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]3)=[CH:30][CH:29]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59751443HCID 59751443, compound

Product 1

HCID 68518335HCID 68518335, compoundYield 599.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring room temperature solution of the product of Example 62 (79 mg, 0.013 mmol) in dimethylformamide (5 mL) add 60% sodium hydride (6 mg, 0.15 mmol). Stir this mixture at ambient temperature for 10 minutes and then add iodomethane (0.014 mL, 0.15 mmol). Stir the reaction for 30 minutes at ambient temperature then quench it with brine. Extract the resulting aqueous mixture into ethyl acetate. Wash the combined extracts with brine; dry (sodium sulfate) and concentrate them in vacuo. Purify the resulting material on a Chromatotron (silica gel; 3%-10% MeOH gradient in CH2Cl2) to obtain 47 mg of the title compound (68%). MS (IS+) m/e 603 (M+1).

Workup

  1. stirringStir
  2. customthe reaction for 30 minutes at ambient temperature
  3. customthen quench it with brine
  4. extractionExtract the resulting aqueous mixture into ethyl acetate
  5. washWash the combined extracts with brine
  6. dry with materialdry (sodium sulfate)
  7. concentrationconcentrate them in vacuo
  8. customPurify the resulting material on a Chromatotron (silica gel; 3%-10% MeOH gradient in CH2Cl2)

Sources & evidence

ORD record
ord-858e443ac2214e7ea81c24b24709e2fb
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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