Hydrochloric Acid → HCID 22134554, compound

HRID 350619Notes

Reaction equation

HRID 350619 reaction equation
C[O:2][C:3](=[O:21])[C:4]([NH:6][C:7]1[CH:12]=[C:11]([NH:13]C(=O)C)[CH:10]=[CH:9][C:8]=1[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:5].[Li+].[OH-].Cl>O1CCOCC1>[NH2:13][C:11]1[CH:10]=[CH:9][C:8]([C:17]([CH3:20])([CH3:19])[CH3:18])=[C:7]([NH:6][C:4](=[O:5])[C:3]([OH:21])=[O:2])[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 23577005HCID 23577005, compound

Product 1

HCID 22134554HCID 22134554, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of N-(5-Acetylamino-2-tert-butyl-phenyl)-oxalamic acid methyl ester (1.28 g, 4.38 mmol) in 1,4-Dioxane (5 mL) at room temperature was added 1.05 equiv of 1.0N LiOH (4.60 mL, 4.60 mmol). After stirring at room temperature for 30 min, the reaction mixture was treated with 0.5N HCl (20 mL), stirred for 5 min and then partitioned between EtOAc/water. The organic phase was washed with saturated NaCl solution (50 mL), dried over Na2SO4 and evaporated to dryness. The oily residue was recrystallized from CH2Cl2/Hexane to give the title compound as a white fine crystal (1.74 g, 96%). 1HNMR (DMSO-d6) δ 10.05 (s, 1H), 9.96 (s, 1H), 7.50 (d, J=2.1 Hz, 1H), 7.42 (dd, J=9.0, 2.1 Hz, 1H), 7.33 (d, J=8.7 Hz, 1H), 2.02 (s, 3H), 1.30 (s, 9H); MS(ES) for C14H18N2O4 (MW=278.30): negative 277 ([M−H]−).

Workup

  1. stirringstirred for 5 min
  2. custompartitioned between EtOAc/water
  3. washThe organic phase was washed with saturated NaCl solution (50 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe oily residue was recrystallized from CH2Cl2/Hexane

Sources & evidence

ORD record
ord-898d7020acc5417a86d9079e17a8b553
Source dataset
uspto-grants-2007_02
Patent number
US07183260B2

Reaction notes

Loading…