Ethanol → 1-Acetylamino-11-benzyloxy-1,1-diethoxycarbonylundecane

HRID 1934572Notes

Reaction equation

HRID 1934572 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].C([CH:10](CC)[C:11]([NH2:13])=[O:12])C.[O-][CH2:17][CH3:18].[Na+].[CH2:20]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]I)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:39](O)[CH3:40]>>[C:11]([NH:13][C:2]([C:1]([O:7][CH2:17][CH3:18])=[O:6])([C:3]([O:5][CH2:39][CH3:40])=[O:4])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][O:27][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:12])[CH3:10]

Participants

5

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 137127691-Benzyloxy-10-iododecaneHCID 22466969Diethyl acetamide malonate

Product 1

HCID 224670111-Acetylamino-11-benzyloxy-1,1-diethoxycarbonylundecaneYield 89.7%

Procedure

Anhydrous ethanol (10.5 ml) and diethylacetamide malonate (2661 mg, 12.25 mmols) were added to sodium ethoxide (834 mg, 12.25 mmols). After stirring for 10 minutes, 1-benzyloxy-10-iododecane (Compound q-1) (2661 mg, 12.25 mmols) was added to the mixture. The mixture was heated to reflux for 4 hours and concentrated in vacuo. Chloroform (200 ml) and water (100 ml) were added to the residue for separation. The organic layer was washed with saturated sodium chloride aqueous solution (100 ml), dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (300 ml, hexane:ethyl acetate=4:1) to give Compound (r-2) (5080 mg, yield: 89.7%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated in vacuo
  4. additionChloroform (200 ml) and water (100 ml) were added to the residue for separation
  5. washThe organic layer was washed with saturated sodium chloride aqueous solution (100 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (300 ml, hexane:ethyl acetate=4:1)
  9. customto give Compound (r-2) (5080 mg, yield: 89.7%)

Sources & evidence

ORD record
ord-78d2e175a8964d72bbfa64e91fb6ac82
Source dataset
uspto-grants-2002_05
Patent number
US06384063B1

Reaction notes

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