Methyl iodide → HCID 22725270, compound

HRID 1016658Notes

Reaction equation

HRID 1016658 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[O:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH:25]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[NH:27][CH2:26]4)[CH2:19][CH2:18]3)[C:11]=2[O:10][CH2:9][CH2:8]1.[C:34](O)(=O)C(O)=O.C(O)(=O)C(O)=O.O1C2C=CC=C(N3CCN(CCC4C5C(=CC=CC=5)NC4)CC3)C=2OCC1.[H-].[Na+].IC.C(OCC)(=O)C>O1CCCC1>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[O:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH:25]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]([CH3:34])[CH2:26]4)[CH2:19][CH2:18]3)[C:11]=2[O:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 131723627HCID 131723627, compound

Product 1

HCID 22725270HCID 22725270, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4a (1.5 g) in dry tetrahydrofuran (50 mL) was added dropwise to a suspension of sodium hydride (60% in mineral oil, 0.21 g) in tetrahydrofuran (25 mL) at room temperature. After stirring for 30 min a solution of iodomethane (0.75 g) in dry tetrahydrofuran (25 mL) was added dropwise. Stirring for 1 hour followed by standard work-up with ethyl acetate gave an oil which was purified by flash chromatography (eluent: heptane/ethyl acetate/triethylamine 15:3:2). The resulting oil was converted to the title oxalate salt (0.3 g) from acetone by addition of oxalic acid. Mp 155-65° C. 1H NMR (DMSO-d6) 1.75-1.85 (m, 1H); 2.05-2.15 (m, 1H); 2.70 (s, 3H); 2.90-3.25 (m, 12H); 3.40 (t, 1H); 4.15-4.30 (m, 4H); 6.45-6.55 (m, 3H); 6.65 (t, 1H); 6.75 (t, 1H); 7.05 (t, 1H); 7.10 (d, 1H). MS m/z (%): 380 (MH+, 4%), 178 (4%), 132 (53%).

Workup

  1. additionwas added dropwise
  2. customgave an oil which
  3. customwas purified by flash chromatography (eluent: heptane/ethyl acetate/triethylamine 15:3:2)
  4. additionThe resulting oil was converted to the title oxalate salt (0.3 g) from acetone by addition of oxalic acid

Sources & evidence

ORD record
ord-41c892abb90147f4820ff10d1b10b249
Source dataset
uspto-grants-2002_11
Patent number
US06476035B1

Reaction notes

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