Diethylamine → HCID 22099390, compound

HRID 1457579Notes

Reaction equation

HRID 1457579 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]1([N:22]([CH2:42][CH2:43][CH2:44][C:45]([OH:47])=O)[C:23](=[O:41])[NH:24][C:25]2[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:26]=2[O:27][CH2:28][O:29][CH3:30])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O[N:49]1[C:53](=O)[CH2:52][CH2:51][C:50]1=O.C(NCC)C>C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C.O1CCCC1>[C:16]1([N:22]([CH2:42][CH2:43][CH2:44][C:45]([N:49]([CH2:53][CH3:52])[CH2:50][CH3:51])=[O:47])[C:23](=[O:41])[NH:24][C:25]2[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([C:37]([CH3:39])([CH3:40])[CH3:38])[C:26]=2[O:27][CH2:28][O:29][CH3:30])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

9

Reactant 4

HCID 8021DiethylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 22099401HCID 22099401, compound

Product 1

HCID 22099390HCID 22099390, compoundYield 70.3%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice-cooling, 2.5 g of 1,3-dicyclohexylcarbodiimide (DCC) was added to a mixture of 5.0 g of {2-[3-phenyl-3-(3-carboxypropyl)ureido]-4-methoxy-6-tert-butyl-phenoxy}methoxymethane, 1.4 g of N-hydroxysuccinimide (HOSu) and 50 ml of tetrahydrofuran (THF). The mixture was stirred at room temperature for 5 hours. Insoluble materials were filtered off and the filtrate was condensed. Under ice-cooling, a mixed solution of 1.2 ml of diethylamine and 10 ml of dimethylformamide (DMF) was added dropwise to a mixture of the obtained residue, 1.9 ml of tri-ethylamine and 10 ml of DMF. The resulting mixture was stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture and the mixture was washed and dried, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=1:2) to give 3.95 g of {2-[3-phenyl-3-(3-diethylaminocarbonylpropyl)ureido]-4-methoxy-6-tert-butylphenoxy}methoxymethane (yield: 70%, state: pale yellow oily product, IR: 3340, 1676, 1635, 1590, 1519 cm-1).

Workup

  1. temperatureUnder ice-cooling
  2. filtrationInsoluble materials were filtered off
  3. customcondensed
  4. temperatureUnder ice-cooling
  5. stirringThe resulting mixture was stirred at room temperature overnight
  6. washthe mixture was washed
  7. customdried
  8. customthe solvent was removed under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-8bb39d4a003c4999ac21f9e0e9cc8cdf
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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