Acetic Anhydride → 7-{Acetyl[4-(acetyloxy)nonyl]amino}heptanoic acid
Reaction equation
[OH:1][CH:2]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:3][CH2:4][CH2:5][N:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:7](=[O:9])[CH3:8].[C:24](OC(=O)C)(=[O:26])[CH3:25]>C(OCC)C>[C:24]([O:1][CH:2]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:3][CH2:4][CH2:5][N:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:7](=[O:9])[CH3:8])(=[O:26])[CH3:25]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 7-[N-(4-hydroxynonyl)acetamido]-heptanoic acid (9.8 g., 0.03 mole) (Example 1, Step C) and acetic anhydride (6.1 g., 0.06 mole) is heated at 60° C. for 18 hours. The mixture is cooled and taken up in 80 ml. of ethyl ether. The solution is extracted with and ice-cold solution of 8 g. of sodium hydroxide in 150 ml. of water. The basic solution is separated and acidified with concentrated hydrochloric acid. The crude product that separates is extracted into ether, washed with water and dried over sodium sulfate. The ether is evaporated and the residual oil is purified by chromatoraphy on slica gel using 2% methanol in chloroform as the eluting solvent. There is obtained 7-[N-(4-acetoxynonyl)acetamido]heptanoic acid as a viscous oil.
Workup
- temperatureThe mixture is cooled
- extractionThe solution is extracted with and ice-cold solution of 8 g
- customThe basic solution is separated
- extractionThe crude product that separates is extracted into ether
- washwashed with water
- dry with materialdried over sodium sulfate
- customThe ether is evaporated
- customthe residual oil is purified by chromatoraphy on slica gel
Sources & evidence
- ORD record
- ord-3cf42250a16b4ffcb89a28cc30b7260e
- Source dataset
- uspto-grants-1976_10
- Patent number
- US03987091
Reaction notes
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