Acetic Anhydride → HCID 20327652, compound

HRID 372534Notes

Reaction equation

HRID 372534 reaction equation
[OH:1][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][CH2:5][N:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[S:7]([CH3:10])(=[O:9])=[O:8].[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(OCC)C>[C:25]([O:1][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][CH2:5][N:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[S:7]([CH3:10])(=[O:8])=[O:9])(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9885481HCID 9885481, compound

Product 1

HCID 20327652HCID 20327652, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7-[N-(4-hydroxynonyl)methanesulfonamido]heptanoic acid (10.9 g., 0.03 mole) (Example 1, Step B) and acetic anhydride (6.1 g., 0.06 mole) is heated at 60° C. for 18 hours. The mixture is cooled and 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 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 chromatography on silica gel using 2% methanol in chloroform as the eluting solvent. There is obtained 7-[N-(4-acetoxynonyl)methanesulfonamido]heptanoic acid as a viscous oil.

Workup

  1. temperatureThe mixture is cooled
  2. extractionThe solution is extracted with an ice-cold solution of 8 g
  3. customThe basic solution is separated
  4. extractionThe crude product that separates is extracted into ether
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customThe ether is evaporated
  8. customthe residual oil is purified by chromatography on silica gel using 2% methanol in chloroform as the eluting solvent

Sources & evidence

ORD record
ord-87a23dd6e5744a24aa8abb12b3ffec74
Source dataset
uspto-grants-1978_05
Patent number
US04091107

Reaction notes

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