2,4-Dimethoxyphenyl isocyanate → Ethyl 2-(4-{2-[3-(2,4-dimethoxyphenyl)-1-heptylureido]ethyl}phenoxy)-2-methylpropionate

HRID 2258022Notes

Reaction equation

HRID 2258022 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:25]=[CH:24][C:14]([O:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:26][O:27][C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[N:36]=[C:37]=[O:38]>C(Cl)Cl>[CH3:26][O:27][C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[NH:36][C:37](=[O:38])[N:8]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:24][CH:25]=1)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 6016372,4-Dimethoxyphenyl isocyanateHCID 23192930Ethyl 2-[4-(heptylaminoethyl)phenoxy]-2-methylpropionate

Product 1

HCID 22924175Ethyl 2-(4-{2-[3-(2,4-dimethoxyphenyl)-1-heptylureido]ethyl}phenoxy)-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step (d) (2.1 g) and 2,4-dimethoxyphenylisocyanate (1.1 g, Aldrich) were dissolved in CH2Cl2 (50 ml). The resulting solution was stirred at room temperature for 17 hours and then evaporated in vacuo. The residue was flash chromatographed through a silica column using hexanes/CH2C1 /EtOAc (50:25:25) as eluant to give the desired product as a very light brown oil (2.0 g).

Workup

  1. customevaporated in vacuo
  2. customchromatographed through a silica column

Sources & evidence

ORD record
ord-c033c022daa94816a823a761b469f875
Source dataset
uspto-grants-1997_08
Patent number
US05658944

Reaction notes

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