Methyl iodide → HCID 52949871, compound

HRID 1594014Notes

Reaction equation

HRID 1594014 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:8]([CH2:27][CH2:28][CH2:29][OH:30])[N:9]2[C:14]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:10]2)=[O:5])[CH3:2].CI.[CH3:38]COCC.CCCCCC>CC#N>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:8]([CH2:27][CH2:28][CH2:29][O:30][CH3:38])[N:9]2[C:14]=1[C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)=[N:10]2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 21584099Diethylether hexaneHCID 52943384HCID 52943384, compound

Product 1

HCID 52949871HCID 52949871, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 41 (10.4 mg, 0.022 mmol), MeI (24 μL, 0.389 mmol), and Ag2O (25 mg, 0.108 mmol) in CH3CN (1 mL) was heated at 80° C. for 24 h. The reaction mixture was filtered through celite and washed with CH2Cl2. The filtrate was concentrated in vacuo and purified by TLC (silica gel, 35% EtOAc/hexane) to provide a yellow oil. The oil was sonicated in 2:1 Et2O/hexane to provide the title compound as an off-white solid. 1H NMR (DMSO-d6) δ 0.88 (t, J=7.1 Hz, 3H), 1.21 (t, J=7.1 Hz, 3H), 1.87 (m, 2H), 3.20 (m, 2H), 3.21 (s, 3H), 3.52 (m, 8H), 3.72 (m, 4H), 4.17 (q, J=7.1 Hz, 2H), 6.77 (s, 1H), 7.40 (m, 2H), 7.46 (m, 3H). Mass Spectrum (ESI+) m/e=496.2 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with CH2Cl2
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by TLC (silica gel, 35% EtOAc/hexane)
  5. customto provide a yellow oil

Sources & evidence

ORD record
ord-f2701cce3e0a4e6590026e8461b9d14f
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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