Sodium Hydroxide → HCID 9888510, compound

HRID 2294238Notes

Reaction equation

HRID 2294238 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]/[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[S:9][CH:10]=1)C.[OH-].[Na+]>C1COCC1>[O:30]=[C:12]([NH:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][C:4]([OH:31])=[O:3])[N:7]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]/[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 88230762HCID 88230762, compound

Product 1

HCID 9888510HCID 9888510, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the above ester (7.4 g, 16.5 mmol) and sodium hydroxide (1.44 g, 36.1 mmol) was combined in THF (150 mL) and cooled in ice under N2 atmosphere. Enough distilled water was added portionwise until the hydroxide was dissolved (~15 mL) and the mixture was maintained at 0° for 2 h, then allowed to warm to ambient temperatures with stirring for 15 h. The reaction mixture was evaporated in vaccuo, the residue cooled in ice and treated with 2M aqueous HCl solution with stirring. The whim precipitate was collected by vacuum filtration, washed with water and air dried. This material was crystallized from boiling heptane, filtered hot, and dried overnight on an abderhalden apparatus (refluxing acetone) to give 4.6 g of the title compound as a white powder, mp 116°-118° C.

Workup

  1. temperaturecooled in ice under N2 atmosphere
  2. distillationEnough distilled water
  3. additionwas added portionwise until the hydroxide
  4. dissolutionwas dissolved (~15 mL)
  5. temperaturethe mixture was maintained at 0° for 2 h
  6. temperatureto warm to ambient temperatures
  7. customThe reaction mixture was evaporated in vaccuo
  8. temperaturethe residue cooled in ice
  9. additiontreated with 2M aqueous HCl solution
  10. stirringwith stirring
  11. filtrationThe whim precipitate was collected by vacuum filtration
  12. washwashed with water and air
  13. customdried
  14. customThis material was crystallized
  15. filtrationfiltered hot
  16. dry with materialdried overnight on an abderhalden apparatus (refluxing acetone)

Sources & evidence

ORD record
ord-01b4e1c69d4743689d75848461a528ee
Source dataset
uspto-grants-1997_11
Patent number
US05688821

Reaction notes

Loading…