Iodoethane → HCID 54153301, compound

HRID 843126Notes

Reaction equation

HRID 843126 reaction equation
O1CC[CH2:3][CH2:2]1.[CH2:6]([O:8][C:9]([C:11]1[O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][CH2:24][N:25]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:26]([CH3:29])([CH3:28])[CH3:27])[C:14]=2[C:15]=1[CH3:16])=[O:10])[CH3:7].C([N-]C(C)C)(C)C.[Li+].C(I)C>C(OCC)(=O)C>[CH2:6]([O:8][C:9]([C:11]1[O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][CH2:24][N:25]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[C:26]([CH3:27])([CH3:28])[CH3:29])[C:14]=2[C:15]=1[CH2:16][CH2:2][CH3:3])=[O:10])[CH3:7]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 54327483HCID 54327483, compound

Product 1

HCID 54153301HCID 54153301, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a dry tetrahydrofuran (3 ml) solution of 4-[3-(tert-butoxycarbonyl-tert-butyl-amino)-propoxy]-3-methyl-benzofuran-2-carboxylic acid ethyl ester (50 mg) was added lithium diisopropylamide (1.2 ml, 0.5N in THF) at −78° C. After 30 minutes ethyl iodide (160 μl) was added at the same temperature. Then reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated ammonium chloride solution and dried over anhydrous sodium sulfate then concentrated in vacuo to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane-methanol to give 4-[3-(tert-butoxycarbonyl-tert-butyl-amino)-propoxy]-3-propyl-benzofuran-2-carboxylic acid ethyl ester as a pale yellow oil (5.1 mg). FAB-MS: m/z 462 (MH+); 1H-NMR (CDCl3): δ 1.12-1.54 (21H, m), 2.09 (2H, m), 2.75 (3H, s), 3.52 (2H, dd, J=7.6 Hz, 9.9 Hz), 4.09 (2H, t, J=5.9 Hz), 4.43 (2H, q, J=7.3 Hz), 6.61 (1H, d, J=7.9 Hz), 7.12 (1H, d, J=8.6 Hz), 7.31 (1H, dd, J=8.6 Hz, 7.9 Hz).

Workup

  1. customThen reaction mixture
  2. washwashed with saturated ammonium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationthen concentrated in vacuo to dryness
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1cf6437d59e34f2bb1bedee995b015d8
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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