Hydrochloric Acid → HCID 54339358, compound

HRID 843129Notes

Reaction equation

HRID 843129 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:15][CH2:16][CH2:17][O:18][C:19]1[C:24]2[C:25]([CH2:31][OH:32])=[C:26]([C:28]([OH:30])=[O:29])[O:27][C:23]=2[CH:22]=[CH:21][CH:20]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].CI.Cl>CN(C=O)C>[CH3:1][O:29][C:28]([C:26]1[O:27][C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([O:18][CH2:17][CH2:16][CH2:15][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:13])[C:33]([CH3:36])([CH3:35])[CH3:34])[C:24]=2[C:25]=1[CH2:31][OH:32])=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22615114HCID 22615114, compound

Product 1

HCID 54339358HCID 54339358, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of potassium carbonate (4.0 mg) and 4-[3-(tert-butoxycarbonyl-tert-butyl-amino)-propoxy]-3-hydroxymethyl-benzofuran-2-carboxylic acid (5.0 mg) in dry DMF (0.8 ml) was added methyl iodide (48 μl) at room temperature and the mixture was stirred overnight. The solvent was evaporated in vacuo to give the crude material as a white heavy syrup, which was then treated with 0.1N HCl (10 ml). The product was extracted with ethyl acetate (10 ml) three times and washed with saturated sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography developed by hexane-ethyl acetate to give 4-[3-(tert-butoxycarbonyl-tert-butyl-amino)-propoxy]-3-hydroxymethyl-benzofuran-2-carboxylic acid methyl ester (3.7 mg) as a white solid. FAB-MS: m/z 436 (MH+); 1H-NMR (CDCl3): δ 1.42-1.48 (18H, m), 2.11 (2H, quintet, J=7.3 Hz), 3.54 (2H, t, J=7.3 Hz), 4.07 (1H, t, J=6.9 Hz), 4.12 (2H, t, J=7.3 Hz), 4.48 (3H, s), 5.22 (2H, d, J=6.9 Hz), 6.68 (1H, d, J=7.9 Hz), 7.18 (1H, d, J=7.9 Hz), 7.40 (1H, dd, J=7.9 Hz, 7.9 Hz).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give the crude material as a white heavy syrup, which
  3. extractionThe product was extracted with ethyl acetate (10 ml) three times
  4. washwashed with saturated sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-335f1529e714425da152a6ef6abc2e3e
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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