Sodium Hydroxide → HCID 22994060, compound

HRID 1167825Notes

Reaction equation

HRID 1167825 reaction equation
C(OC1C(N)=C([C:15]2[N:19]=[C:18]([C:20]3[S:24][C:23]([NH:25][C:26]4[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=4)=[N:22][C:21]=3[NH2:38])[O:17][N:16]=2)C=CC=1C(O)=O)(C)(C)C.[OH-].[Na+]>FC(F)(F)C(O)=O.ClCCl>[NH2:25][C:26]1[CH:27]=[C:28]([C:15]2[N:19]=[C:18]([C:20]3[S:24][C:23]([NH:25][C:26]4[CH:27]=[C:28]([O:36][CH3:37])[C:29]([O:34][CH3:35])=[C:30]([O:32][CH3:33])[CH:31]=4)=[N:22][C:21]=3[NH2:38])[O:17][N:16]=2)[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22993949HCID 22993949, compound

Product 1

HCID 22994060HCID 22994060, compoundYield 189%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 267 mg (0.49 mmol) of 3-(3-t-butyloxycarboxy-aminophenyl)-5-[2-[(3,4,5-trimethoxyphenyl)amino]-4-amino-5-thiazolyl]-1,2,4-oxadiazole (prepared according to Example B(2)) in 3 mL of 50% trifluoroacetic acid in dichloromethane was stirred for 60 minutes at ambient temperature and then poured onto ice. 3N NaOH was added dropwise until the solution was basic, and the mixture was extracted with EtOAc. The organic layer was washed with NaHCO3 and brine, and dried over Na2SO4. The solvent was removed to yield 204 mg (95% yield) of the title compound as a light yellow solid.

Workup

  1. customwas stirred for 60 minutes at ambient temperature
  2. additionpoured onto ice
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic layer was washed with NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-3dcb3d5b79a44b7ca3ea6ef8877c9e2f
Source dataset
uspto-grants-2003_09
Patent number
US06620828B2

Reaction notes

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