Sodium Hydroxide → HCID 16065089, compound

HRID 1991137Notes

Reaction equation

HRID 1991137 reaction equation
C([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH:18]=3)[N:13](S(C3C=CC=CC=3)(=O)=O)[CH:12]=2)[N:10]=1)=[O:5])C.[OH-].[Na+]>CCO>[CH2:20]([C:17]1[CH:18]=[C:19]2[C:11]([C:9]3[N:10]=[C:6]([C:4]([OH:5])=[O:3])[S:7][CH:8]=3)=[CH:12][NH:13][C:14]2=[N:15][CH:16]=1)[CH:21]([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59128675HCID 59128675, compound

Product 1

HCID 16065089HCID 16065089, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 81 (412 mg, 0.99 mmol) in EtOH (10 mL) was added 10% aqueous NaOH (5 mL) and the reaction mixture heated to reflux. After 2 h, the solution was cooled to r.t., and the mixture concentrated to 5 mL under reduced pressure. Acetic acid was then added dropwise with stirring until a precipitate appeared, which was filtered off and dried to afford 82 (267 mg, 0.89 mmol, 90%) as a yellow powder. 1H NMR (400 MHz, DMSO-d6) δ 0.91 (d, J=6.6 Hz, 2H), 1.92 (nonet, J=6.6 Hz, 1H), 2.60 (d, J=7.2 Hz, 2H), 7.69 (s, 1H), 7.95 (s, 1H), 8.08 (d, J=1.9 Hz, 1H), 8.27 (s, 1H), 11.73 (s, 1H).

Workup

  1. temperaturethe reaction mixture heated to reflux
  2. concentrationthe mixture concentrated to 5 mL under reduced pressure
  3. additionAcetic acid was then added dropwise
  4. filtrationwhich was filtered off
  5. customdried

Sources & evidence

ORD record
ord-f40f03c247e94a0e874318bcbabc017b
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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