HCID 57763203, compound → HCID 57763241, compound

HRID 230834Notes

Reaction equation

HRID 230834 reaction equation
[CH:1]1([S:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[C:13]([C:19]([O:21]CC)=[O:20])[C:12]3=[O:24])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[OH-].[Na+]>[CH:1]1([S:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[C:13]([C:19]([OH:21])=[O:20])[C:12]3=[O:24])(=[O:8])=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 57763203HCID 57763203, compound

Product 1

HCID 57763241HCID 57763241, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Intermediate 5 (10.9 g) was dissolved in ethanol (100 ml) and 2M sodium hydroxide (100 ml), and the mixture was heated under reflux for 3 h. After cooling, the solvent was evaporated in vacuo and the residue was dissolved in water and washed with ethyl acetate. The aqueous layer was acidified with 2M hydrochloric acid to between pH 5 and pH 6 which caused a precipitate to form. The precipitate was filtered off, washed with water, and dried in vacuo overnight to give the title compound as a beige solid (9.47 g).

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. customthe solvent was evaporated in vacuo
  4. dissolutionthe residue was dissolved in water
  5. washwashed with ethyl acetate
  6. customto form
  7. filtrationThe precipitate was filtered off
  8. washwashed with water
  9. customdried in vacuo overnight

Sources & evidence

ORD record
ord-4b8b43f589d0490daf0eac580cc7a683
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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