Triethylamine → HCID 14373558, compound

HRID 2291731Notes

Reaction equation

HRID 2291731 reaction equation
[OH:1][CH:2]([CH2:22][N:23]([CH2:34][CH2:35][CH3:36])[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:21])[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12]2)=[CH:7][CH:6]=1.[C:37]1([CH:43]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:44](Cl)=[O:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:47]1([CH:43]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:44]([O:1][CH:2]([CH2:22][N:23]([CH2:34][CH2:35][CH3:36])[C:24]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])[CH2:3][O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9](=[O:21])[CH:10]=[C:11]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:12]3)=[CH:7][CH:6]=2)=[O:45])[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 746372,2-Diphenylacetyl chlorideHCID 14373557HCID 14373557, compound

Product 1

HCID 14373558HCID 14373558, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7-[2-hydroxy-3-[N-(benzyloxycarbonyl)-propylamino]propoxy]flavone in crude form (5.09 g, 11 mmol), diphenylacetyl chloride (10.20 g, 44 mmol), and triethylamine (19.0 ml, 136 mmol) in toluene (65 ml) was refluxed under nitrogen for 18 hr. Toluene was removed by evaporation and the oily residue was dissolved in chloroform, washed twice with saturated NaHCO3 and once with water, and then dried (K2CO3). The dried solution, upon evaporation, gave a brown oil which was purified by HPLC (Water Associates PrepLC/Systems 500) using 3% acetone/CH2Cl2 that contained a small amount of NH4OH. A tan syrup of the title compound was obtained; 5.57 g (76% yield).

Workup

  1. temperaturewas refluxed under nitrogen for 18 hr
  2. customToluene was removed by evaporation
  3. dissolutionthe oily residue was dissolved in chloroform
  4. washwashed twice with saturated NaHCO3 and once with water
  5. dry with materialdried (K2CO3)
  6. customThe dried solution, upon evaporation
  7. customgave a brown oil which
  8. customwas purified by HPLC (Water Associates PrepLC/Systems 500)

Sources & evidence

ORD record
ord-9c85eeb83d1049dabef1a43f56999052
Source dataset
uspto-grants-1989_01
Patent number
US04797498

Reaction notes

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