Acetic Anhydride → 7-[2-(3-Acetyloxyoctyl)-4-oxo-3-thiazolidinyl]heptanoic Acid

HRID 867121Notes

Reaction equation

HRID 867121 reaction equation
[OH:1][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][CH:5]1[N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:19])[CH2:7][S:6]1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(OCC)(=O)C>[C:25]([O:1][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][CH:5]1[N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:19])[CH2:7][S:6]1)(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 203173917-[2-(3-Hydroxyoctyl)-4-oxo-3-thiazolidinyl]heptanoic acid

Product 1

HCID 203174197-[2-(3-Acetyloxyoctyl)-4-oxo-3-thiazolidinyl]heptanoic Acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7-[2-(3-hydroxyoctyl)-4-oxo-3-thiazolidinyl]heptanoic acid (9.0 g., 0.025 mole) and acetic anhydride (6.1 g., 0.06 mole) is heated at 60° C. for 18 hours. The resulting mixture is cooled to room temperature and dissolved in ethyl acetate providing a clear solution which is extracted with an ice-cold solution of sodium hydroxide (8 g.) in water (150 ml.). The basic solution is quickly separated and acidified with concentrated hydrochloric acid. The oily acid which separates is extracted with ether. The organic extract is washed with water, dried over sodium sulfate, and filtered. Evaporation of the filtrate in vacuo at 40° to 50° C. leaves a residual oil which is purified via application to a silica gel (150 g.) column with chloroform. Elution with chloroform-methanol (99:1; v:v) provides the title compound as a colorless, viscous oil.

Workup

  1. temperatureThe resulting mixture is cooled to room temperature
  2. extractionis extracted with an ice-cold solution of sodium hydroxide (8 g.) in water (150 ml.)
  3. customThe basic solution is quickly separated
  4. extractionThe oily acid which separates is extracted with ether
  5. extractionThe organic extract
  6. washis washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customEvaporation of the filtrate in vacuo at 40° to 50° C.
  10. customleaves a residual oil which
  11. customis purified via application to a silica gel (150 g.) column with chloroform
  12. washElution with chloroform-methanol (99:1; v:v)

Sources & evidence

ORD record
ord-f8b12f03e10a42cba40a2055f58236e4
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

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