1,2-Dimethoxyethane → N-Decyl-3-(3-[cis-3-methoxycarbonylpropenamido]phenyl)propenamide

HRID 1065809Notes

Reaction equation

HRID 1065809 reaction equation
[CH2:1]([NH:11][C:12](=[O:29])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22](=[O:28])/[CH:23]=[CH:24]\[C:25]([OH:27])=[O:26])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:30]OCCOC.[N+](=C)=[N-]>C(O)(=O)C.CCOCC>[CH2:1]([NH:11][C:12](=[O:29])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22](=[O:28])/[CH:23]=[CH:24]\[C:25]([O:27][CH3:30])=[O:26])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 9550Diazomethane2×HCID 86738051N-Decyl-3-(3-[cis-3-carboxypropenamido]phenyl)propenamide

Product 1

HCID 86738053N-Decyl-3-(3-[cis-3-methoxycarbonylpropenamido]phenyl)propenamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 400 mg. of N-decyl-3-(3-[cis-3-carboxypropenamido]phenyl)propenamide and 15 ml. of 1,2-dimethoxyethane is added a solution of 1.5 mmoles of diazomethane in 5 ml. of ether. The reaction mixture is stirred at room temperature for 16 hours, and then the excess diazomethane is decomposed by the addition of a few drops of acetic acid. The total solvents are removed by evaporation in vacuo, and the residue is dissolved in ethyl acetate. The ethyl acetate solution is washed with 1 N sodium hydroxide, followed by water, followed by saturated sodium chloride solution, and then dried using sodium sulfate. Evaporation of the dried ethyl acetate solution in vacuo affords the title compound.

Workup

  1. additionTo a stirred mixture of 400 mg
  2. customThe total solvents are removed by evaporation in vacuo
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washThe ethyl acetate solution is washed with 1 N sodium hydroxide
  5. customdried
  6. customEvaporation of the dried ethyl acetate solution in vacuo

Sources & evidence

ORD record
ord-e5cf42a29ca44eec9e964491748ce5f1
Source dataset
uspto-grants-1982_05
Patent number
US04331683

Reaction notes

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