Methyl iodide → HCID 53986280, compound

HRID 1637103Notes

Reaction equation

HRID 1637103 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:32])[CH2:8][CH:9]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[CH:19]=1)[C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].[CH3:35]I>C1COCC1.C(OCC)(=O)C>[CH3:35][N:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[C:7](=[O:32])[CH2:8][CH:9]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[CH:19]=1)[C:10]#[C:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15463384HCID 15463384, compound

Product 1

HCID 53986280HCID 53986280, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the compound from Example 22 (0.07 g, 0.16 mmol) in THF (2 mL) under an argon atmosphere was added 60% NaH/mineral oil suspension (0.008 g, 0.19 mmol), followed by methyl iodide (0.012 mL, 0.19 mmol). After heating at 80° C. for 0.25 h, the mixture was cooled to room temperature, was diluted with ethyl acetate, was washed with brine, was dried (MgSO4) and was evaporated. Purification by flash chromatography, eluting with 1:1 hexanes/ethyl acetate provided the title compound as a yellow resin (0.025 g, 34%). Anal. (C27H28N2SO3 ·0.375 H2O) calcd: C, 69.39; H, 6.20; N, 5.99. found: C, 69.52; H, 6.22; N, 5.78.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. washwas washed with brine
  3. dry with materialwas dried (MgSO4)
  4. customwas evaporated
  5. customPurification by flash chromatography
  6. washeluting with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-7fcd70cb21b14392a7dbe1e475a693a9
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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