Sodium Hydroxide → HCID 9888510, compound

HRID 651478Notes

Reaction equation

HRID 651478 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

Conditions

Temperature
0 °C

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° C. for 2 h, then allowed to warm to ambient temperatures with stirring for 15 h. The reaction mixture was evaporated in vacuo, the residue cooled in ice and treated with 2M aqueous HCl solution with stirring. The white 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. temperatureto warm to ambient temperatures
  6. customThe reaction mixture was evaporated in vacuo
  7. temperaturethe residue cooled in ice
  8. additiontreated with 2M aqueous HCl solution
  9. stirringwith stirring
  10. filtrationThe white precipitate was collected by vacuum filtration
  11. washwashed with water and air
  12. customdried
  13. customThis material was crystallized
  14. filtrationfiltered hot
  15. dry with materialdried overnight on an abderhalden apparatus (refluxing acetone)

Sources & evidence

ORD record
ord-7b0fc4f31047419da46b8be2d2207f3b
Source dataset
uspto-grants-2001_08
Patent number
US06281234B1

Reaction notes

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