Water → HCID 50942877, compound

HRID 2045802Notes

Reaction equation

HRID 2045802 reaction equation
[CH3:1][C:2]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH2:14][CH2:15][N:16]1[C@H:21]2[CH2:22][CH2:23][C@@H:17]1[CH2:18][CH:19]([N:24]1[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=[C:25]1[CH3:33])[CH2:20]2)[CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6].[H-].[Na+].I[CH3:43].O>C1COCC1>[CH3:43][N:4]([CH2:3][C:2]([CH3:1])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:14][CH2:15][N:16]1[C@H:21]2[CH2:22][CH2:23][C@@H:17]1[CH2:18][CH:19]([N:24]1[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=[C:25]1[CH3:33])[CH2:20]2)[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 50942876HCID 50942876, compound

Product 1

HCID 50942877HCID 50942877, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title compound from example 19 (65 mg, 0.12 mmol) in dry THF (2 mL) was added sodium hydride (6 mg, 0.14 mmol) as a 60% suspension in mineral oil and the solution stirred under a nitrogen atmosphere at room temperature for 30 min. Iodomethane (0.03 mL, 0.48 mmol) was added and the reaction stirred at room temperature for 1 h. An additional portion of iodomethane (0.02 mL, 0.32 mmol) was added and the solution stirred for 1 h more at room temperature. Water was added and the reaction partitioned between ethyl acetate and water. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 0-4% methanol/CH2Cl2 to afford the title compound (50 mg, 75%) as a white solid.

Workup

  1. stirringthe reaction stirred at room temperature for 1 h
  2. stirringthe solution stirred for 1 h more at room temperature
  3. customthe reaction partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 0-4% methanol/CH2Cl2

Sources & evidence

ORD record
ord-25f96851ba3e448786e925752f05f913
Source dataset
uspto-grants-2013_11
Patent number
US08592395B2

Reaction notes

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