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

HRID 848559Notes

Reaction equation

HRID 848559 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-7e2db68a776e4b8e8ec2b1e7497b051c
Source dataset
uspto-grants-1981_10
Patent number
US04296129

Reaction notes

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