Dimethylformamide → N-(2-acetoacetoxyethyl)N-cyclohexyl-4-(6-carbostyriloxy)butyramide

HRID 1284914Notes

Reaction equation

HRID 1284914 reaction equation
CN(C)C=O.[CH:6]1([N:12]([CH2:30][CH2:31][OH:32])[C:13](=[O:29])[CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH:22]=[CH:21]3)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH2:33]=[C:34]1[O:38][C:36](=[O:37])[CH2:35]1>C(N(CC)CC)C>[C:36]([O:32][CH2:31][CH2:30][N:12]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[C:13](=[O:29])[CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH:22]=[CH:21]2)(=[O:37])[CH2:35][C:34]([CH3:33])=[O:38]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 12661DiketeneHCID 12866343N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramide

Product 1

HCID 20250808N-(2-acetoacetoxyethyl)N-cyclohexyl-4-(6-carbostyriloxy)butyramideYield 69.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 100 ml of dimethylformamide, there were added 7.45 g of N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramide and 0.5 ml of triethylamine, then the whole mixture was heated at 80° to 90° C. on an oil bath. Next, 1.8 g of diketene were added dropwise to the reaction mixture, then the mixture was stirred for 1 hour at the same temperature. The reaction mixture was concentrated then was purified by a silica gel column chromatography (eluant: chloroform/methanol=50/1), and the solvent was removed by distillation under reduced pressure to yield 6.33 g of N-(2-acetoacetoxyethyl)N-cyclohexyl-4-(6-carbostyriloxy)butyramide in the form of a brownish oily substance.

Workup

  1. temperaturethe whole mixture was heated at 80° to 90° C. on an oil bath
  2. concentrationThe reaction mixture was concentrated
  3. customthen was purified by a silica gel column chromatography (eluant: chloroform/methanol=50/1)
  4. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-e85660938ee24dbd953de6b47dce7012
Source dataset
uspto-grants-1986_01
Patent number
US04564619

Reaction notes

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