Potassium Hydroxide → HCID 19029198, compound

HRID 2256009Notes

Reaction equation

HRID 2256009 reaction equation
[C:1]([NH:4][CH:5]([C:10]1([CH3:15])[CH2:14][CH:13]=[CH:12][O:11]1)[C:6]([O:8]C)=[O:7])(=[O:3])[CH3:2].[OH-].[K+]>CCO>[C:1]([NH:4][CH:5]([C:10]1([CH3:15])[CH2:14][CH:13]=[CH:12][O:11]1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19029181HCID 19029181, compound

Product 1

HCID 19029198HCID 19029198, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 95% EtOH solution (150 mL) of 17 (5.00 g, 23.6 mmol) and KOH (3.00 g, 53.5 mmol) was stirred at room temperature (48 h). The solvent was removed and the residue was dissolved in H2O (50 mL). The aqueous solution was washed with Et2O (3×50 mL) and then acidified to pH 1.5 with 10% H3PO4. The acidified solution was extracted with EtOAc (3×200 mL) and the combined extracts were dried (Na2SO4), and concentrated in vacuo to give 2.90 g (62%) of 18: mp 178°-180° C. (d) (recrystallized from CH3CN); IR (KBr) 3400 (br), 1700 (br) cm-1 ; 1H NMR (DMSO-d6) δ 1.67 (s, CH3), 1.83 (s, C(O)CH3), 6.39 (m, C3H, C4H), 7.59 (s, C5H), 8.34 (s, NH), 12.63 (s, C(O)OH); 13C NMR (DMSO-d6) 22.20 (C(O)CH3), 22.59 (CH3), 57.65 (C(CH3)), 107.09 (C4), 110.49 (C3), 142.33 (C5), 153.36 (C2), 168.86 (C(O)NH), 171.78 (C(O)OH) ppm; mass spectrum, m/e (relative intensity) 198 (M+ +1, 4), 143 (97), 152 (63), 140 (23), 111 (73), 110 (100), 94 (24). Anal. (C9H11NO4) C, H, N.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in H2O (50 mL)
  3. washThe aqueous solution was washed with Et2O (3×50 mL)
  4. extractionThe acidified solution was extracted with EtOAc (3×200 mL)
  5. dry with materialthe combined extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff0919adf836448395c1fd8c56c96b10
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

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