Sodium Hydroxide → 3-(2-Acetylamino-3-methylbutyryl)-5-tert-butyl-2,3-dihydro-[1,2,4]thiadiazole-2-carboxylic acid

HRID 900566Notes

Reaction equation

HRID 900566 reaction equation
C([O:3][C:4]([N:6]1[CH:10]([C:11](=[O:20])[CH:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]([CH3:15])[CH3:14])[N:9]=[C:8]([C:21]([CH3:24])([CH3:23])[CH3:22])[S:7]1)=[O:5])C.[OH-].[Na+]>CO>[C:17]([NH:16][CH:12]([CH:13]([CH3:15])[CH3:14])[C:11]([CH:10]1[N:9]=[C:8]([C:21]([CH3:23])([CH3:24])[CH3:22])[S:7][N:6]1[C:4]([OH:5])=[O:3])=[O:20])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 686553483-(2-Acetylamino-3-methyl-butyryl)-5-tert-butyl-2,3-dihydro-[1,2,4]thiadiazole-2-carboxylic Acid Ethyl Ester

Product 1

HCID 186237603-(2-Acetylamino-3-methylbutyryl)-5-tert-butyl-2,3-dihydro-[1,2,4]thiadiazole-2-carboxylic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 38 (0.301 g, 0.84 mmol) in MeOH (10 mL) was added 1N NaOH solution (1.7 mL, 1.7 mmol). The reaction was stirred at room temperature for 2 hours and solvent was evaporated. The residue was dissolved in EtOAc and washed with 0.5N NaHSO4 (2×) and brine and was dried over anhydrous Na2SO4, filtered and evaporated to give the title compound as a yellow solid (0.277 g, quantitative).

Workup

  1. customsolvent was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 0.5N NaHSO4 (2×) and brine
  4. dry with materialwas dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-074dd27f7075454c9cfdf6fa558a135a
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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