Diethyl bromomalonate → 2-[[4-(t-Butoxycarbonylamino-methyl)-benzyl]-(4-dipropylamino-butyl)-amino]-malonic acid diethyl ester

HRID 2080882Notes

Reaction equation

HRID 2080882 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Br[CH:39]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:40]([O:42][CH2:43][CH3:44])=[O:41].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:43]([O:42][C:40](=[O:41])[CH:39]([N:16]([CH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:28])=[CH:14][CH:13]=1)[CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH3:27])[C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH3:44]

Participants

6

Reactant 4

HCID 69637Diethyl bromomalonateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 66941782{4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl Ester

Product 1

HCID 671038582-[[4-(t-Butoxycarbonylamino-methyl)-benzyl]-(4-dipropylamino-butyl)-amino]-malonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (520 mg) obtained in Example 23-4 was dissolved in anhydrous DMF (10 ml) and added with diisopropylethylamine (463 μl) and diethyl bromomalonate (340 μl) and the whole was stirred at room temperature for 2 hours. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added thereto and the whole was stirred for a while. The solution was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (421 mg) as a colorless oily substance.

Workup

  1. customAfter completion of the reaction
  2. stirringthe whole was stirred for a while
  3. extractionThe solution was subjected to extraction with chloroform
  4. washwashed with a saturated saline solution
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-247e9001edf342e3a744cbfc64b0f4f3
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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