Acetic Anhydride → 7-{[4-(Acetyloxy)nonyl](carbamoyl)amino}heptanoic acid

HRID 1729931Notes

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]([NH2:9])=[O: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]([NH2:9])=[O:8])(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 7-[1-(4hydroxynonyl)ureido]heptanoic acid (9.9 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 an ice-cold solution of 8 g. of sodium hydroxide in 150 ml. of water. The basis solution is separated and acidified with concentrated hydrochloric acid. The oil 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 chromatography on silica gel using 2% methanol in chloroform as the eluting solvent. Thus there is obtained 7-[1-(4-acetoxynonyl)ureido] heptanoic acid as a yellow oil.

Workup

temperatureThe mixture is cooled
extractionThe solution is extracted with an ice-cold solution of 8 g
customThe basis solution is separated
extractionThe oil 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 chromatography on silica gel using 2% methanol in chloroform as the eluting solvent

Sources & evidence

ORD record: ord-537c0d46c6654f0a888984f8e49d2622
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03989749

Reaction notes

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