Ethanol → HCID 54423884, compound

HRID 843130Notes

Reaction equation

HRID 843130 reaction equation
[Na].[CH2:2]([O:4][C:5]([C:7]1[O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][N:22]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:23]([CH3:26])([CH3:25])[CH3:24])[C:10]=2[C:11]=1[CH2:12]Br)=[O:6])[CH3:3].[CH2:34]([OH:36])[CH3:35]>>[CH2:2]([O:4][C:5]([C:7]1[O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][N:22]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:23]([CH3:26])([CH3:25])[CH3:24])[C:10]=2[C:11]=1[CH2:12][O:36][CH2:34][CH3:35])=[O:6])[CH3:3]

Participants

4

Reactant 3

HCID 702EthanolHCID 5360545SodiumHCID 54210163HCID 54210163, compound

Product 1

HCID 54423884HCID 54423884, compound

Procedure

To ethanol (2.0 ml) was added sodium metal (15 mg) at room temperature. After 25 minutes, 3-bromomethyl-4-[3-(tert-butoxycarbonyl-tert-butyl-amino)-propoxy]-benzofuran-2-carboxylic acid ethyl ester (98 mg) was added to the reaction mixture. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (10 ml) and water (20 ml). The product was extracted with ethyl acetate (10 ml) 3 times. Organic layer was combined and dried over anhydrous sodium sulfate, concentrated in vacuo to dryness. 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-ethoxymethyl-benzofuran-2-carboxylic acid ethyl ester (70 mg) as a pale yellow oil. FAB-MS: m/z 478 (MH+); 1H-NMR (CDCl3): δ 1.22 (3H, t, J=6.9 Hz), 1.37-1.47 (21H, m), 2.09 (2H, quintet, J=7.3 Hz), 3.54 (2H, t, J=7.3 Hz), 3.62 (2H, q, J=6.9 Hz), 4.12 (2H, t, J=7.3 Hz), 4.45 (2H, q, J=7.3 Hz), 5.06 (2H, s), 6.65 (1H, d, J=7.9 Hz), 7.14 (1H, d, J=7.9 Hz), 7.33 (1H, dd, J=7.9 Hz, 7.9 Hz).

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride solution (10 ml) and water (20 ml)
  2. extractionThe product was extracted with ethyl acetate (10 ml) 3 times
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo to dryness
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b9f02ed2b6fc4ecb93da7a48dc8588a3
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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